U.S. patent application number 13/837990 was filed with the patent office on 2014-01-30 for herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2-carboxylic acid or a derivative thereof and certain sulfonylureas.
This patent application is currently assigned to DOW AGROSCIENCES LLC. The applicant listed for this patent is Richard K. Mann, Norbert M. Satchivi, Paul R. Schmitzer, Carla N. Yerkes. Invention is credited to Richard K. Mann, Norbert M. Satchivi, Paul R. Schmitzer, Carla N. Yerkes.
Application Number | 20140031218 13/837990 |
Document ID | / |
Family ID | 49995435 |
Filed Date | 2014-01-30 |
United States Patent
Application |
20140031218 |
Kind Code |
A1 |
Mann; Richard K. ; et
al. |
January 30, 2014 |
HERBICIDAL COMPOSITIONS COMPRISING
4-AMINO-3-CHLORO-5-FLUORO-6-(4-CHLORO-2-FLUORO-3-METHOXYPHENYL)
PYRIDINE-2-CARBOXYLIC ACID OR A DERIVATIVE THEREOF AND CERTAIN
SULFONYLUREAS
Abstract
Provided herein are synergistic herbicidal compositions
comprising (a) a compound of formula (I): ##STR00001## or an
agriculturally acceptable salt or ester thereof and (b) a
sulfonylurea e.g., amidosulfuron, azimsulfuron, bensulfuron-methyl,
chlorsulfuron, cyclosulfamuron, ethametsulfuron-methyl,
ethoxysulfuron, flazasulfuron, flucetosulfuron,
flupyrsulfuron-methyl sodium, foramsulfuron, imazosulfuron,
iofensulfuron, iodosulfuron-methyl sodium, mesosulfuron-methyl,
metsulfuron-methyl, nicosulfuron, orthosulfamuron,
primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrimisulfan,
pyroxasulfone, rimsulfuron, sulfometuron-methyl, sulfosulfuron,
thifensulfuron-methyl, triafamone, triasulfuron, tribenuron-methyl
or trifloxysulfuron-sodium, or an agriculturally acceptable salt or
ester thereof. The compositions and methods provide control of
undesirable vegetation, e.g., in crops and other settings, e.g., in
direct-seeded, water-seeded and transplanted rice, cereals, wheat,
barley, oats, rye, sorghum, corn or maize, sugarcane, sunflower,
oilseed rape, canola, sugar beet, soybean, cotton, pineapple,
pastures, grasslands, rangelands, fallowland, turf, tree and vine
orchards, aquatics, plantation crops, vegetables, industrial
vegetation management (IVM) or rights-of-way (ROW).
Inventors: |
Mann; Richard K.; (Franklin,
IN) ; Yerkes; Carla N.; (Crawfordsville, IN) ;
Satchivi; Norbert M.; (Westfield, IN) ; Schmitzer;
Paul R.; (Indianapolis, IN) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
Mann; Richard K.
Yerkes; Carla N.
Satchivi; Norbert M.
Schmitzer; Paul R. |
Franklin
Crawfordsville
Westfield
Indianapolis |
IN
IN
IN
IN |
US
US
US
US |
|
|
Assignee: |
DOW AGROSCIENCES LLC
Indianapolis
IN
|
Family ID: |
49995435 |
Appl. No.: |
13/837990 |
Filed: |
March 15, 2013 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
|
61675117 |
Jul 24, 2012 |
|
|
|
Current U.S.
Class: |
504/103 ;
504/130 |
Current CPC
Class: |
A01N 43/40 20130101;
A01N 43/40 20130101; A01N 43/54 20130101; A01N 43/66 20130101; A01N
43/80 20130101; A01N 47/36 20130101 |
Class at
Publication: |
504/103 ;
504/130 |
International
Class: |
A01N 43/40 20060101
A01N043/40 |
Claims
1. A herbicidal composition comprising a herbicidally effective
amount of (a) a compound of the formula (I) ##STR00042## or an
agriculturally acceptable salt or ester thereof and (b) a compound
selected from the group consisting of: amidosulfuron, azimsulfuron,
bensulfuron-methyl, chlorsulfuron, cyclosulfamuron,
ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron,
flucetosulfuron, flupyrsulfuron-methyl sodium, foramsulfuron,
imazosulfuron, iofensulfuron, iodosulfuron-methyl sodium,
mesosulfuron-methyl, metsulfuron-methyl, nicosulfuron,
orthosulfamuron, primisulfuron-methyl, propyrisulfuron,
prosulfuron, pyrimisulfan, pyroxasulfone, rimsulfuron,
sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl,
triafamone, triasulfuron, tribenuron-methyl or
trifloxysulfuron-sodium, or a salt or ester thereof.
2. The composition of claim 1, further comprising a herbicide
safener.
3. The composition of claim 1, further comprising an agriculturally
acceptable adjuvant or carrier.
4. A method of controlling undesirable vegetation which comprises
contacting the vegetation or the locus thereof with or applying to
the soil or water to prevent the emergence or growth of vegetation
the composition of claim 1.
5. A method of controlling undesirable vegetation which comprises
contacting the vegetation or the locus thereof with or applying to
the soil or water to prevent the emergence or growth of vegetation
a herbicidally effective amount of (a) a compound of the formula
(I) ##STR00043## or an agriculturally acceptable salt or ester
thereof and (b) a compound selected from the group consisting of:
amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorsulfuron,
cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron,
flazasulfuron, flucetosulfuron, flupyrsulfuron-methyl sodium,
foramsulfuron, imazosulfuron, iofensulfuron, iodosulfuron-methyl
sodium, mesosulfuron-methyl, metsulfuron-methyl, nicosulfuron,
orthosulfamuron, primisulfuron-methyl, propyrisulfuron,
prosulfuron, pyrimisulfan, pyroxasulfone, rimsulfuron,
sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl,
triafamone, triasulfuron, tribenuron-methyl or
trifloxysulfuron-sodium, or a salt or ester thereof.
6. The method of claim 5, wherein the undesirable vegetation is
controlled in direct-seeded, water-seeded and transplanted rice,
cereals, wheat, barley, oats, rye, sorghum, corn/maize, sugarcane,
sunflower, oilseed rape, canola, sugar beet, soybean, cotton,
pineapple, pastures, grasslands, rangelands, fallowland, turf, tree
and vine orchards, aquatics, plantation crops, vegetables,
industrial vegetation management (IVM) or rights-of-way (ROW).
7. The method of claim 5, wherein the undesirable vegetation is
immature.
8. The method of claim 5, wherein the (a) and (b) are applied to
water.
9. The method of claim 8, wherein the water is part of a flooded
rice paddy.
10. The method of claim 8, wherein the (a) and (b) are applied
pre-emergently to the weed or the crop.
11. The method of claim 8, wherein the (a) and (b) are applied
post-emergently to the weed or the crop.
12. The method of claim 8, wherein the undesirable vegetation is
controlled in glyphosate-, 5-enolpyruvylshikimate-3-phosphate
(EPSP) synthase inhibitor-, glufosinate-, glutamine synthetase
inhibitor-, dicamba-, phenoxy carboxylic acid auxin-, pyridine
carboxylic acid auxin-, synthetic auxin-, auxin transport
inhibitor-, aryloxyphenoxypropionates-, cyclohexanedione-,
phenylpyrazoline-, acetyl CoA carboxylase (ACCase) inhibitor-,
imidazolinone-, sulfonylurea-, pyrimidinylthiobenzoate-,
triazolopyrimidine-, sulfonylaminocarbonyltriazolinone-,
acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS)
inhibitor-, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-,
phytoene desaturase inhibitor-, carotenoid biosynthesis inhibitor-,
protoporphyrinogen oxidase (PPO) inhibitor-, cellulose biosynthesis
inhibitor-, mitosis inhibitor-, microtubule inhibitor-, very long
chain fatty acid inhibitor-, fatty acid and lipid biosynthesis
inhibitor-, photosystem I inhibitor-, photosystem II inhibitor-,
triazine-, or bromoxynil-tolerant crop.
13. The method of claim 8, wherein the tolerant crop possesses
multiple or stacked traits conferring tolerance to multiple
chemistries or inhibitors of multiple modes of action.
14. The method of claim 8 wherein the undesirable vegetation
comprises a herbicide resistant or tolerant weed.
15. The method of claim 14, wherein the resistant or tolerant weed
is a biotype with resistance or tolerance to multiple herbicides,
multiple chemical classes, inhibitors of multiple herbicide
modes-of-action or via multiple resistance mechanisms.
16. The method of claim 14 wherein the resistant or tolerant weed
is a biotype resistant or tolerant to acetolactate synthase (ALS)
or acetohydroxy acid synthase (AHAS) inhibitors, photosystem II
inhibitors, acetyl CoA carboxylase (ACCase) inhibitors, synthetic
auxins, auxin transport inhibitors, photosystem I inhibitors,
5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors,
microtubule assembly inhibitors, fatty acid and lipid synthesis
inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, carotenoid
biosynthesis inhibitors, very long chain fatty acid (VLCFA)
inhibitors, phytoene desaturase (PDS) inhibitors, glutamine
synthetase inhibitors, 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD)
inhibitors, mitosis inhibitors, cellulose biosynthesis inhibitors,
herbicides with multiple modes-of-action, quinclorac,
arylaminopropionic acids, difenzoquat, endothall, or
organoarsenicals.
Description
PRIORITY CLAIM
[0001] This application claims the benefit of U.S. provisional
patent application No. 61/675,117 filed on Jul. 24, 2012, this
provisional application is incorporated herein by reference in its
entirety.
FIELD
[0002] Provided herein are herbicidal compositions comprising, as
well as methods of controlling undersirable vegetation utilizing:
(a)
4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-
-carboxylic acid or an agriculturally acceptable ester or salt
thereof and (b) a sulfonylurea selected from the group consisting
of amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorsulfuron,
cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron,
flazasulfuron, flucetosulfuron, flupyrsulfuron-methyl sodium,
foramsulfuron, imazosulfuron, iofensulfuron, iodosulfuron-methyl
sodium, mesosulfuron-methyl, metsulfuron-methyl, nicosulfuron,
orthosulfamuron, primisulfuron-methyl, propyrisulfuron,
prosulfuron, pyrimisulfan, pyroxasulfone, rimsulfuron,
sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl,
triafamone, triasulfuron, tribenuron-methyl and
trifloxysulfuron-sodium, or an agriculturally acceptable salt or
ester thereof.
BACKGROUND
[0003] The protection of crops from weeds and other vegetation
which inhibit crop growth is a constantly recurring problem in
agriculture. To help combat this problem, researchers in the field
of synthetic chemistry have produced an extensive variety of
chemicals and chemical formulations effective in the control of
such unwanted growth. Chemical herbicides of many types have been
disclosed in the literature and a large number are in commercial
use. However, there remains a need for compositions and methods
that are effective in controlling undesirable vegetation.
SUMMARY
[0004] A first embodiment of the invention provided herein includes
herbicidal compositions comprising an herbicidally effective amount
of (a) a compound of the formula (I)
##STR00002##
or an agriculturally acceptable salt or ester thereof, and (b) at
least one a sulfonylurea and agriculturally acceptable salts and
esters thereof.
[0005] A second embodiment includes the mixture of the first
embodiment in which of formula (I), is present in the form of at
least one of the following forms: a carboxylic acid, a carboxylate
salt, an aralkyl, an alkyl ester, an unsubstituted benzyl, a
substituted benzyl, a C.sub.1-4 alkyl, and/or an n-butyl ester.
[0006] A third embodiment includes the mixture according to either
the first or second embodiments wherein the (b) at least one
sulfonylurea selected from the group consisting of: amidosulfuron,
azimsulfuron, bensulfuron-methyl, chlorsulfuron, cyclosulfamuron,
ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron,
flucetosulfuron, flupyrsulfuron-methyl sodium, foramsulfuron,
imazosulfuron, iofensulfuron, iodosulfuron-methyl sodium,
mesosulfuron-methyl, metsulfuron-methyl, nicosulfuron,
orthosulfamuron, primisulfuron-methyl, propyrisulfuron,
prosulfuron, pyrimisulfan, pyroxasulfone, rimsulfuron,
sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl,
triafamone, triasulfuron, tribenuron-methyl or
trifloxysulfuron-sodium, or an agriculturally acceptable salt,
carboxylic acid, carboxylate salt, or ester thereof of at least one
of the aforementioned dimethoxy-pyrimidines.
[0007] A fourth embodiment includes the mixtures according to any
of the first, second, or third embodiments in which the
sulfonylurea in the mixture is amidosulfuron wherein the weight
ratio of the compound of formula (I) to amidosulfuron given in
units of gae/ha to gai/ha or gae/ha to gae/ha is selected from the
group of ranges of ratios and ratios consisting of about: 1:1.1 or
within any range defined between any pair of the foregoing
values.
[0008] A fifth embodiment includes the mixtures according to any of
the first, second, or third embodiments in which the sulfonylurea
in the mixture is azimsulfuron wherein the weight ratio of the
compound of formula (I) to azimsulfuron given in units of gae/ha to
gai/ha or gae/ha to gae/ha is selected from the group of ranges of
ratios and ratios consisting of about: 1:4.1, 1:1.4, 1:2.9, 3.5:1,
7:1, 2.8:1, 1:5.7, 14:1, from 1:5.7 to 7:1, from 1.4:1 to 1:2.9,
from 2.8:1 to 1:1.4, from 3.5:1 to 14:1, from 1.4:1 to 2.8:1, from
14:1 to 1:5.7, or within any range defined between any pair of the
foregoing values.
[0009] A sixth embodiment includes the mixtures according to any of
the first, second, or third embodiments in which the sulfonylurea
in the mixture is bensulfuron-methyl wherein the weight ratio of
the compound of formula (I) to bensulfuron-methyl given in units of
gae/ha to gai/ha or gae/ha to gae/ha is selected from the group of
ranges of ratios and ratios consisting of about: 1.4:1, 2.8:1,
1:1.4, 4.4:1, 1:1, 1:2, 1:4, 1:8, 1:16, 3:1, 2:1, 1:1.7, 1:1.5,
1:4.4, 5.5:1, 1:2.2, 1:8.8, from 1.4:1 to 5.5:1, from 1:2.2 to
1:8.8, from 2.8:1 to 1:1.4, from 1:4 to 2:1, from 1:1 to 1:8, from
1:2 to 1:8, from 4.4:1 to 1:16, from 3:1 to 1:16, from 1:16 to
5.5:1, or within any range defined between any pair of the
foregoing values.
[0010] A seventh embodiment includes the mixtures according to any
of the first, second, or third embodiments in which the
sulfonylurea in the mixture is chlorsulfuron wherein the weight
ratio of the compound of formula (I) to chlorsulfuron given in
units of gae/ha to gai/ha or gae/ha to gae/ha is selected from the
group of ranges of ratios and ratios consisting of about: 4:1, or
within any range defined between any pair of the foregoing
values.
[0011] An eighth embodiment includes the mixtures according to any
of the first, second, or third embodiments in which the
sulfonylurea in the mixture is cyclosulfamuron wherein the weight
ratio of the compound of formula (I) to cyclosulfamuron given in
units of gae/ha to gai/ha or gae/ha to gae/ha is selected from the
group of ranges of ratios and ratios consisting of about: 1:1.6,
1.3:1, 2.6:1, from 1:1.6 to 2.6:1, from 1.3:1 to 1:1.6, or within
any range defined between any pair of the foregoing values.
[0012] A ninth embodiment includes the mixtures according to any of
the first, second, or third embodiments in which the sulfonylurea
in the mixture is ethametsulfuron-methyl wherein the weight ratio
of the compound of formula (I) to ethametsulfuron-methyl given in
units of gae/ha to gai/ha or gae/ha to gae/ha is selected from the
group of ranges of ratios and ratios consisting of about: from 1:15
to 68:1, from 1:9 to 8:1, or within any range defined between any
pair of the foregoing values.
[0013] A tenth embodiment includes the mixtures according to any of
the first, second, or third embodiments in which the sulfonylurea
in the mixture is ethoxysulfuron wherein the weight ratio of the
compound of formula (I) to ethoxysulfuron given in units of gae/ha
to gai/ha or gae/ha to gae/ha is selected from the group of ranges
of ratios and ratios consisting of about: 1.1:1, 1:1.9, 1:3.8,
1:8.8, 1:4.4, 2.1:1, 2.3:1, 1.2:1, 1.4:1, 2.8:1, 5.7:1, 1:1.7,
1:3.4, from 2.3:1 to 1.2:1, from 1:1.7 to 1:3.4, from 1.4:1 to
5.7:1, from 2.1:1 to 1:1.9, from 2.1:1 to 1:8.8, from 5.7:1 to
1:8.8, or within any range defined between any pair of the
foregoing values.
[0014] An eleventh embodiment includes the mixtures according to
any of the first, second, or third embodiments in which the
sulfonylurea in the mixture is flazasulfuron wherein the weight
ratio of the compound of formula (I) to flazasulfuron given in
units of gae/ha to gai/ha or gae/ha to gae/ha is selected from the
group of ranges of ratios and ratios consisting of about: 1:3.1,
1:6.3, 1:12.5, 1.3:1, and from 1:3.1 to 1:12.5, or within any range
defined between any pair of the foregoing values.
[0015] A twelfth embodiment includes the mixtures according to any
of the first, second, or third embodiments in which the
sulfonylurea in the mixture is flucetosulfuron wherein the weight
ratio of the compound of formula (I) to flucetosulfuron given in
units of gae/ha to gai/ha or gae/ha to gae/ha is selected from the
group of ranges of ratios and ratios consisting of about: 350:1,
175:1, 88:1, 44:1, 22:1, 19:1, 8.8:1, 3.2:1, 1.6:1, 1:1.25, 9.4:1,
4.7:1, 6.4:1, from 88:1 to 350:1, from 4.7:1 to 19.1, from 1:125 to
3.2:1, from 350:1 to 22.1; and from 350:1 to 1:1.25, or within any
range defined between any pair of the foregoing values.
[0016] A thirteenth embodiment includes the mixtures according to
any of the first, second, or third embodiments in which the
sulfonylurea in the mixture is flupyrsulfuron-methyl sodium wherein
the weight ratio of the compound of formula (I) to
flupyrsulfuron-methyl sodium given in units of gae/ha to gai/ha or
gae/ha to gae/ha is selected from the group of ranges of ratios and
ratios consisting of about: 1.75:1, or within any range defined
between any pair of the foregoing values.
[0017] A fourteenth embodiment includes the mixtures according to
any of the first, second, or third embodiments in which the
sulfonylurea in the mixture is foramsulfuron wherein the weight
ratio of the compound of formula (I) to foramsulfuron given in
units of gae/ha to gai/ha or gae/ha to gae/ha is selected from the
group of ranges of ratios and ratios consisting of about: 1:2.5,
1:5, from 1:2.5 to 1:5, or within any range defined between any
pair of the foregoing values.
[0018] A fifteenth embodiment includes the mixtures according to
any of the first, second, or third embodiments in which the
sulfonylurea in the mixture is imazosulfuron wherein the weight
ratio of the compound of formula (I) to imazosulfuron given in
units of gae/ha to gai/ha or gae/ha to gae/ha is selected from the
group of ranges of ratios and ratios consisting of about: 1:1.2,
1:2.4, 1:4.8, 1:9.6, 1:19, 1:56, 1:38, 1:1.3, 1:2.6, 1:5.1, 1:10.3,
from 1:1.3 to 1.5:1, from 1:2.6 to 1:38, from 1:19 to 1:56, from
1:1.2 to 1:56, from 1:1.2 to 1:2.4, and from 1:1.2 to 1:9.6, or
within any range defined between any pair of the foregoing
values.
[0019] A sixteenth embodiment includes the mixtures according to
any of the first, second, or third embodiments in which the
sulfonylurea in the mixture is iodosulfuron-methyl sodium wherein
the weight ratio of the compound of formula (I) to
iodosulfuron-methyl sodium given in units of gae/ha to gai/ha or
gae/ha to gae/ha is selected from the group of ranges of ratios and
ratios consisting of about: 1.6:1, 3.2:1, 3.5:1, 6.4:1, 12.8:1, and
from 1.6:1 to 12.8:1, or within any range defined between any pair
of the foregoing values.
[0020] A seventeenth embodiment includes the mixtures according to
any of the first, second, or third embodiments in which the
sulfonylurea in the mixture is iofensulfuron wherein the weight
ratio of the compound of formula (I) to iofensulfuron given in
units of gae/ha to gai/ha or gae/ha to gae/ha is selected from the
group of ranges of ratios and ratios consisting of about: 1:25 to
about 600:1, from about 1:9 to about 75:1, or within any range
defined between any pair of the foregoing values.
[0021] A eighteenth embodiment includes the mixtures according to
any of the first, second, or third embodiments in which the
sulfonylurea in the mixture is mesosulfuron-methyl wherein the
weight ratio of the compound of formula (I) to mesosulfuron-methyl
given in units of gae/ha to gai/ha or gae/ha to gae/ha is selected
from the group of ranges of ratios and ratios consisting of about:
1:8 to 300:1, from 1:2 to 50:1, from 1:1 to 8:1, from 2:1 to 4:1,
2.9:1, or within any range defined between any pair of the
foregoing values.
[0022] A nineteenth embodiment includes the mixtures according to
any of the first, second, or third embodiments in which the
sulfonylurea in the mixture is metsulfuron-methyl wherein the
weight ratio of the compound of formula (I) to metsulfuron-methyl
given in units of gae/ha to gai/ha or gae/ha to gae/ha is selected
from the group of ranges of ratios and ratios consisting of about:
1:1.7, 1.2:1, 2.3:1, 1:3.4, 1.4:1, 2.8:1, 5.6:1, 8:1, from 1.4:1 to
5.6:1, from 1:3.4 to 8:1, from 1:3.4 to 2.3:1, or within any range
defined between any pair of the foregoing values.
[0023] A twentieth embodiment includes the mixtures according to
any of the first, second, or third embodiments in which the
sulfonylurea in the mixture is nicosulfuron wherein the weight
ratio of the compound of formula (I) to nicosulfuron given in units
of gae/ha to gai/ha or gae/ha to gae/ha is selected from the group
of ranges of ratios and ratios consisting of about: 1.2:1, 2.4:1,
1:1, 1:2, 1:4, 1:1.7, 1:3.3, 1:6.6, 2.4:1, from 2.4 to 1:6.6, and
from 1:1.7 to 1:6.6, from 1:1.7 to 2.4:1, from 1.2:1 to 1:3.3, from
1:1 to 1:4, from 2.4:1 to 1:6.6, or within any range defined
between any pair of the foregoing values.
[0024] A twenty-first embodiment includes the mixtures according to
any of the first, second, or third embodiments in which the
sulfonylurea in the mixture is orthosulfamuron wherein the weight
ratio of the compound of formula (I) to orthosulfamuron given in
units of gae/ha to gai/ha or gae/ha to gae/ha is selected from the
group of ranges of ratios and ratios consisting of about: 1:1.7,
1.2:1, 1:3.4, 2.3:1, 1:6.9, 1:1.4, 1.4:1, from 1:1.4 to 1.4:1, from
1:1.7 to 1.2:1, from 1:1 to 1:6.9, from 1:3.4 to 2.3:1, and from
1:1.7 to 1:6.9, or within any range defined between any pair of the
foregoing values.
[0025] A twenty-second embodiment includes the mixtures according
to any of the first, second, or third embodiments in which the
sulfonylurea in the mixture is primisulfuron-methyl wherein the
weight ratio of the compound of formula (I) to primisulfuron-methyl
given in units of gae/ha to gai/ha or gae/ha to gae/ha is selected
from the group of ranges of ratios and ratios consisting of about:
1:1.9, 1:3.8, and from 1:1.9 to 1:3.8, or within any range defined
between any pair of the foregoing values.
[0026] A twenty-third embodiment includes the mixtures according to
any of the first, second, or third embodiments in which the
sulfonylurea in the mixture is propyrisulfuron wherein the weight
ratio of the compound of formula (I) to propyrisulfuron given in
units of gae/ha to gai/ha or gae/ha to gae/ha is selected from the
group of ranges of ratios and ratios consisting of about: 1:2.6,
1:5.1, 1:10.3, 1:1.3, 1:1.4, 1.4:1, 2.8:1, 1:2.8, 1:5.6, from
1:10.3 to 2.8:1, from 1:5.6 to 2.8:1, from 1:2.6 to 1:10.3, or
within any range defined between any pair of the foregoing
values.
[0027] A twenty-fourth embodiment includes the mixtures according
to any of the first, second, or third embodiments in which the
sulfonylurea in the mixture is prosulfuron wherein the weight ratio
of the compound of formula (I) to prosulfuron given in units of
gae/ha to gai/ha or gae/ha to gae/ha is selected from the group of
ranges of ratios and ratios consisting of about: 1:20 to about
68:1, from about 1:14 to about 8:1, or within any range defined
between any pair of the foregoing values.
[0028] A twenty-fifth embodiment includes the mixtures according to
any of the first, second, or third embodiments in which the
sulfonylurea in the mixture is pyrimisulfan wherein the weight
ratio of the compound of formula (I) to pyrimisulfan given in units
of gae/ha to gai/ha or gae/ha to gae/ha is selected from the group
of ranges of ratios and ratios consisting of about: 1:100 to about
30:1, from about 1:45 to about 10:1, or within any range defined
between any pair of the foregoing values.
[0029] A twenty-sixth embodiment includes the mixtures according to
any of the first, second, or third embodiments in which the
sulfonylurea in the mixture is pyroxasulfone wherein the weight
ratio of the compound of formula (I) to pyroxasulfone given in
units of gae/ha to gai/ha or gae/ha to gae/ha is selected from the
group of ranges of ratios and ratios consisting of about: from
about 1:500 to about 3:1, from about 1:136 to about 1:2, or within
any range defined between any pair of the foregoing values.
[0030] A twenty-seventh embodiment includes the mixtures according
to any of the first, second, or third embodiments in which the
sulfonylurea in the mixture is rimsulfuron wherein the weight ratio
of the compound of formula (I) to rimsulfuron given in units of
gae/ha to gai/ha or gae/ha to gae/ha is selected from the group of
ranges of ratios and ratios consisting of about: 1:1, 4:1, 2:1,
1:2, 1.2:1, 2.4:1, 4.8:1, 9.7:1, 1:1.7, 1:2, 8:1, from 1:1.7 to
9.7:1, from 1:2 to 4:1, from 1:1.7 to 4.8:1, and from 1:2 to 8:1,
or within any range defined between any pair of the foregoing
values.
[0031] A twenty-eighth embodiment includes the mixtures according
to any of the first, second, or third embodiments in which the
sulfonylurea in the mixture is sulfometuron-methyl wherein the
weight ratio of the compound of formula (I) to sulfometuron-methyl
given in units of gae/ha to gai/ha or gae/ha to gae/ha is selected
from the group of ranges of ratios and ratios consisting of about:
1:4.4, 1:2.2, and 1:1.1, or within any range defined between any
pair of the foregoing values.
[0032] A twenty-ninth embodiment includes the mixtures according to
any of the first, second, or third embodiments in which the
sulfonylurea in the mixture is sulfosulfuron wherein the weight
ratio of the compound of formula (I) to sulfosulfuron given in
units of gae/ha to gai/ha or gae/ha to gae/ha is selected from the
group of ranges of ratios and ratios consisting of about: 1:1, or
within any range defined between any pair of the foregoing
values.
[0033] A thirtieth embodiment includes the mixtures according to
any of the first, second, or third embodiments in which the
sulfonylurea in the mixture is thifensulfuron-methyl wherein the
weight ratio of the compound of formula (I) to
thifensulfuron-methyl given in units of gae/ha to gai/ha or gae/ha
to gae/ha is selected from the group of ranges of ratios and ratios
consisting of about: 2.3:1, or within any range defined between any
pair of the foregoing values.
[0034] A thirty-first embodiment includes the mixtures according to
any of the first, second, or third embodiments in which the
sulfonylurea in the mixture is triafamone wherein the weight ratio
of the compound of formula (I) to triafamone given in units of
gae/ha to gai/ha or gae/ha to gae/ha is selected from the group of
ranges of ratios and ratios consisting of about: from 1:25 to 60:1,
from 1:23 to 30:1, or within any range defined between any pair of
the foregoing values.
[0035] A thirty-second embodiment includes the mixtures according
to any of the first, second, or third embodiments in which the
sulfonylurea in the mixture is triasulfuron wherein the weight
ratio of the compound of formula (I) to triasulfuron given in units
of gae/ha to gai/ha or gae/ha to gae/ha is selected from the group
of ranges of ratios and ratios consisting of about: 1:15 to 136:1,
from 1:7 to 16:1, or within any range defined between any pair of
the foregoing values.
[0036] A thirty-third embodiment includes the mixtures according to
any of the first, second, or third embodiments in which the
sulfonylurea in the mixture is tribenuron-methyl wherein the weight
ratio of the compound of formula (I) to tribenuron-methyl given in
units of gae/ha to gai/ha or gae/ha to gae/ha is selected from the
group of ranges of ratios and ratios consisting of about: 4:1, or
within any range defined between any pair of the foregoing
values.
[0037] A thirty-fourth embodiment includes the mixtures according
to any of the first, second, or third embodiments in which the
sulfonylurea in the mixture is trifloxysulfuron-sodium. wherein the
weight ratio of the compound of formula (I) to
trifloxysulfuron-sodium. given in units of gae/ha to gai/ha or
gae/ha to gae/ha is selected from the group of ranges of ratios and
ratios consisting of about: 1:3, 1:1.5, 1.3:1, and from 1:3 to
1.3:1, or within any range defined between any pair of the
foregoing values.
[0038] A thirty-fifth embodiment includes any composition according
to any of the first through the thirty-fourth embodiments wherein
the mixture further comprises at least one an agriculturally
acceptable agent selected from the group consisting of an
adjuvant.
[0039] A thirty-sixth embodiment includes any composition according
to any of the first through the thirty-fifth embodiments wherein
the mixture further comprises at least one an agriculturally
acceptable agent selected from the group consisting of a carrier,
or a safener.
[0040] A thirty-seventh embodiment includes any composition
according to any of the first through the thirty-sixth embodiments
wherein the mixture further comprises at least one an
agriculturally acceptable agent selected from the group consisting
of a safener.
[0041] A thirty-eighth embodiment includes any composition
according to any of the first through the thirty-fourth embodiments
wherein the mixture further comprises at least one an
agriculturally acceptable agent selected from the group consisting
of an adjuvant, a carrier, or a safener.
[0042] A thirty-ninth embodiment includes methods of controlling
undesirable vegetation comprising the steps of applying or
otherwise contacting vegetation and/or soil, and/or water with a
herbicidally effective amount of at least one mixture according to
any of the first through the thirty-eighth embodiments.
[0043] A fortieth embodiment includes methods according to the
tenth embodiment wherein undesirable vegetation is controlled
according to at least technique selected from the group consisting
of: direct-seeded, water-seeded, and/or transplanted rice, cereals,
wheat, barley, oats, rye, sorghum, corn/maize, sugarcane,
sunflower, oilseed rape, canola, sugar beet, soybean, cotton,
pineapple, pastures, grasslands, rangelands, fallowland, turf, tree
and vine orchards, aquatics, plantation crops, vegetables,
industrial vegetation management (IVM), or rights-of-way (ROW).
[0044] A forty-first embodiment includes methods according to
either of the thirty-ninth and fortieth embodiments wherein a
herbicidally effective amount of the mixture is applied post
emergently to at least one of the following: a crop, a field, a
ROW, or a paddy.
[0045] A forty-second embodiment includes methods according to
either of the thirty-ninth and fortieth embodiments wherein a
herbicidally effective amount of the mixture is applied
pre-emergently to at least one of the following: a crop, a field, a
ROW, or a paddy.
[0046] A forty-third embodiment includes methods according to any
of the thirty-ninth through forty-second embodiments wherein a
herbicidally effective amount of the mixture is applied either pre-
or post emergently to at least one of the following: a crop, a
field, a ROW, or a paddy.
[0047] A forty-fourth embodiment includes methods according to any
of the forty-first through the forty-third embodiments wherein the
undesirable vegetation controlled by an application of a
herbicidally effective amount of the mixture and at least one of
the following phytotoxic actives: glyphosate-,
5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitor-,
glufosinate-, glutamine synthetase inhibitor-, dicamba-, phenoxy
auxin-, pyridyloxy auxin-, synthetic auxin-, auxin transport
inhibitor-, aryloxyphenoxypropionate-, cyclohexanedione-,
phenylpyrazoline-, acetyl CoA carboxylase (ACCase) inhibitor-,
imidazolinone-, sulfonylurea-, pyrimidinylthiobenzoate-,
triazolopyrimidine-, sulfonylaminocarbonyltriazolinone-,
acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS)
inhibitor-, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-,
phytoene desaturase inhibitor-, carotenoid biosynthesis inhibitor-,
protoporphyrinogen oxidase (PPO) inhibitor-, cellulose biosynthesis
inhibitor-, mitosis inhibitor-, microtubule inhibitor-, very long
chain fatty acid inhibitor-, fatty acid and lipid biosynthesis
inhibitor-, photosystem I inhibitor-, photosystem II inhibitor-,
protoporphyrinogen oxidase (PPO) inhibitor-, triazine-, or
bromoxynil-tolerant crops.
[0048] A forty-fifth embodiment includes a at least one method
according to any of the forty-first through the forty-fourth
embodiments wherein a plant that is tolerant to at least one
herbicide is treated, and where the tolerant crop possesses
multiple or stacked traits conferring tolerance to multiple
herbicides or inhibitors of multiple modes of action, in some
embodiments the treated plant that expresses resistance to a
herbicide is a itself undesirable vegetation.
[0049] A forty-sixth embodiment includes methods according to the
forty-fifth embodiment, wherein the resistant or tolerant weed is a
biotype with resistance or tolerance to multiple herbicides,
multiple chemical classes, inhibitors of multiple herbicide
modes-of-action, or via multiple resistance mechanisms.
[0050] A forty-seventh embodiment includes at least one of the
methods according to either the forty-fifth or forty-sixth
embodiments, wherein the resistant or tolerant undesirable plant is
a biotype resistant or tolerant to at least on agent selected from
the groups consisting of: acetolactate synthase (ALS) inhibitors or
acetohydroxy acid synthase (AHAS), photosystem II inhibitors,
acetyl CoA carboxylase (ACCase) inhibitors, synthetic auxins, auxin
transport inhibitors, photosystem I inhibitors,
5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors,
microtubule assembly inhibitors, fatty acid and lipid synthesis
inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, carotenoid
biosynthesis inhibitors, very long chain fatty acid (VLCFA)
inhibitors, phytoene desaturase (PDS) inhibitors, glutamine
synthetase inhibitors, 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD)
inhibitors, mitosis inhibitors, cellulose biosynthesis inhibitors,
herbicides with multiple modes-of-action, quinclorac,
arylaminopropionic acids, difenzoquat, endothall, or
organoarsenicals.
[0051] A forty-eighth embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the fourth embodiment wherein the amount of the mixture is applied
at a rate, expressed in gai/ha or gae/ha of amidosulfuron selected
from the group of rates and ranges of rates consisting of about: 10
or within any range defined between any pair of the foregoing
values.
[0052] A forty-ninth embodiment includes methods according to
either of the fourth and forty-eighth embodiments wherein the
controlled plant is at least one plant selected from the group
consisting of: GALAP, LAMPU, VERDE, still other embodiments include
controlling plants from the genera consisting of: Galium, Lamium,
Veronica.
[0053] A fiftieth embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the fifth embodiment wherein the amount of the mixture is applied
at a rate, expressed in gai/ha or gae/ha of azimsulfuron selected
from the group of rates and ranges of rates consisting of about:
2.5, 3.13, 5, 6.25, 12.5, 25, 3.13 to 12.5, and 2.5 to 25, or
within any range defined between any pair of the foregoing
values.
[0054] A fifty-first embodiment includes methods according to
either of the fifth and fiftieth embodiments wherein the controlled
plant is at least one plant selected from the group consisting of:
BRAPP, LEFCH, SCPMA, and ECHOR, still other embodiments include
controlling plants from the genera consisting of: Brachiaria,
Leptochloa, Schoenoplectus, Bolboschoenus, Echinochloa.
[0055] A fifty-second embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the sixth embodiment wherein the amount of the mixture is applied
at a rate, expressed in gai/ha or gae/ha of bensulfuron-methyl
selected from the group of rates and ranges of rates consisting of
about: 3.125, 6.25, 4.38, 8.75, 17.5, 35, 70, from 3.125 to 6.25,
from 4.38 to 17.5, and from 4.38 to 35, or within any range defined
between any pair of the foregoing values.
[0056] A fifty-third embodiment includes methods according to
either of the sixth and fifty-second embodiments wherein the
controlled plant is at least one plant selected from the group
consisting of: ECHOR, LEFCH, BRAPP, ECHCG, ISCRU, SCPMA, still
other embodiments include controlling plants from the genera
consisting of: Echinochloa, Leptochloa, Brachiaria, Ischaemum,
Schoenoplectus, Bolboschoenus.
[0057] A fifty-fourth embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the seventh embodiment wherein the amount of the mixture is applied
at a rate, expressed in gai/ha or gae/ha of chlorsulfuron selected
from the group of rates and ranges of rates consisting of about:
2.2 or within any range defined between any pair of the foregoing
values.
[0058] A fifty-fifth embodiment includes methods according to
either of the seventh and fifty-fourth embodiments wherein the
controlled plant is at least one plant selected from the group
consisting of: VIOTR, CIRAR, still other embodiments include
controlling plants from the genera consisting of: Viola,
Cirsium.
[0059] A fifty-sixth embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the eighth embodiment wherein the amount of the mixture is applied
at a rate, expressed in gai/ha or gae/ha of cyclosulfamuron
selected from the group of rates and ranges of rates consisting of
about: 12.5, or within any range defined between any pair of the
foregoing values.
[0060] A fifty-seventh embodiment includes methods according to
either of the eighth and fifty-sixth embodiments wherein the
controlled plant is at least one plant selected from the group
consisting of: CYPIR, SCPMA, still other embodiments include
controlling plants from the genera consisting of: Cirsium,
Schoenoplectus, Bolboschoenus.
[0061] A fifty-eighth embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the ninth embodiment wherein the amount of the mixture is applied
at a rate, expressed in gai/ha or gae/ha of ethametsulfuron-methyl
selected from the group of rates and ranges of rates consisting of
about: from 6 to 300, from 7 to 55, or within any range defined
between any pair of the foregoing values.
[0062] A fifth-ninth embodiment includes methods according to
either of the ninth and fifty-eighth embodiments used in
herbicidally effective rates for controlling the growth of
undesirable plants that have a negative impact on the growth of
various crop plants.
[0063] A sixtieth embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the tenth embodiment wherein the amount of the mixture is applied
at a rate, expressed in gai/ha or gae/ha of ethoxysulfuron selected
from the group of rates and ranges of rates consisting of about:
7.5, 15, 30, from 7.5 to 15, and from 7.5 to 30, or within any
range defined between any pair of the foregoing values.
[0064] A sixty-first embodiment includes methods according to
either of the tenth and sixtieth embodiments wherein the controlled
plant is at least one plant selected from the group consisting of:
CYPIR, BRAPP, ISCRU, ECHOR, LEFCH still other embodiments include
controlling plants from the genera consisting of: Cyperus,
Brachiaria, Ischaemum, Echinochloa, Leptochloa.
[0065] A sixty-second embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the eleventh embodiment wherein the amount of the mixture is
applied at a rate, expressed in gai/ha or gae/ha of flazasulfuron
selected from the group of rates and ranges of rates consisting of
about: 25, 50, 100, from 25 to 50, from 50 to 100, and from 25 to
100, or within any range defined between any pair of the foregoing
values.
[0066] A sixty-third embodiment includes methods according to
either of the eleventh and sixty-second embodiments wherein the
controlled plant is at least one plant selected from the group
consisting of: IPOHE, LEFCH, still other embodiments include
controlling plants from the genera consisting of: Ipomoea,
Leptochloa.
[0067] A sixty-fourth embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the twelfth embodiment wherein the amount of the mixture is applied
at a rate, expressed in gai/ha or gae/ha of flucetosulfuron
selected from the group of rates and ranges of rates consisting of
about: 0.05, 0.10, 0.20, 1.7, 5, 10, from 0.05 to 0.20, from 5 to 0
10, and from 0.05 to 10, or within any range defined between any
pair of the foregoing values.
[0068] A sixth-fifth embodiment includes methods according to
either of the twelfth and sixty-fourth embodiments wherein the
controlled plant is at least one plant selected from the group
consisting of: LEFCH, IPOHE, CYPIR, BRAPP, and SCPSU, still other
embodiments include controlling plants from the genera consisting
of: Ipomoea, Leptochloa, Cyperus, Brachiaria, Schoenoplectus,
Bolboschoenus.
[0069] A sixty-sixth embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the thirteenth embodiment wherein the amount of the mixture is
applied at a rate, expressed in gai/ha or gae/ha of
flupyrsulfuron-methyl sodium selected from the group of rates and
ranges of rates consisting of about: 5 or within any range defined
between any pair of the foregoing values.
[0070] A sixty-seventh embodiment includes methods according to
either of the thirteenth and sixty-sixth embodiments wherein the
controlled plant is at least one plant selected from the group
consisting of: VERPE, CIRAR, still other embodiments include
controlling plants from the genera consisting of: Veronica,
Cirsium.
[0071] A sixty-eighth embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the fourteenth embodiment wherein the amount of the mixture is
applied at a rate, expressed in gai/ha or gae/ha of foramsulfuron
selected from the group of rates and ranges of rates consisting of
about: 20, 40, and from 20 to 40, or within any range defined
between any pair of the foregoing values.
[0072] A sixty-ninth embodiment includes methods according to
either of the fourteenth and sixty-eighth embodiments wherein the
controlled plant is at least one plant selected from the group
consisting of: LEFCH, still other embodiments include controlling
plants from the genera consisting of: Leptochloa.
[0073] A seventieth embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the fifteenth embodiment wherein the amount of the mixture is
applied at a rate, expressed in gai/ha or gae/ha of imazosulfuron
selected from the group of rates and ranges of rates consisting of
about: 21, 42, 84, 22.5, 45, 168, from 22.5 to 168, from 21 to 42,
or within any range defined between any pair of the foregoing
values.
[0074] A seventy-first embodiment includes methods according to
either of the fifteenth and seventieth embodiments wherein the
controlled plant is at least one plant selected from the group
consisting of: DIGSA, LEFCH, ECHCO, SCPMA, still other embodiments
include controlling plants from the genera consisting of:
Digitaria, Leptochloa, Echinochloa, Schoenoplectus,
Bolboschoenus.
[0075] A seventy-second embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the sixteenth embodiment wherein the amount of the mixture is
applied at a rate, expressed in gai/ha or gae/ha of
iodosulfuron-methyl sodium selected from the group of rates and
ranges of rates consisting of about: 5, 2.5, and from 2.5 to 5, or
within any range defined between any pair of the foregoing
values.
[0076] A seventy-third embodiment includes methods according to
either of the sixteenth and seventy-second embodiments wherein the
controlled plant is at least one plant selected from the group
consisting of: IPOHE, VIOTR, MATCH, CIRAR, still other embodiments
include controlling plants from the genera consisting of: Ipomoea,
Viola, Chamomilla, Cirsium.
[0077] A seventy-fourth embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the seventeenth embodiment wherein the amount of the mixture is
applied at a rate, expressed in gai/ha or gae/ha of iofensulfuron
selected from the group of rates and ranges of rates consisting of
about: from 315 to 3, from 10 to 65, from 1 to 15, from 2 to 300,
from 1 to 8, from 3.5 to 20, from 2 to 4, from 7 to 10, from 3 to
8.75, 3, or within any range defined between any pair of the
foregoing values.
[0078] A seventy-fifth embodiment includes methods according to
either of the seventeenth and seventy-fourth used in herbicidally
effective rates for controlling the growth of undesirable plants
that have a negative impact on the growth of various crop
plants.
[0079] A seventy-sixth embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the eighteenth embodiment wherein the amount of the mixture is
applied at a rate, expressed in gai/ha or gae/ha of
mesosulfuron-methyl selected from the group of rates and ranges of
rates consisting of about: 8.75, from 3, 2 to 4, or within any
range defined between any pair of the foregoing values.
[0080] A seventy-seventh embodiment includes methods according to
either of the eighteenth and seventy-sixth embodiments wherein the
controlled plant is at least one plant selected from the group
consisting of: VERPE, MATCH, CIRAR, still other embodiments include
controlling plants from the genera consisting of: Veronica,
Chamomilla, Cirsium.
[0081] A seventy-eighth embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the nineteenth embodiment wherein the amount of the mixture is
applied at a rate, expressed in gai/ha or gae/ha of
metsulfuron-methyl selected from the group of rates and ranges of
rates consisting of about: 7.5, 15, 1.1, from 1.1 to 15, from 7.5
to 15, or within any range defined between any pair of the
foregoing values.
[0082] A seventy-ninth embodiment includes methods according to
either of the ninteenth and seventy-eighth embodiments wherein the
controlled plant is at least one plant selected from the group
consisting of: BRAPP, ECHOR, MATCH, CIRAR, still other embodiments
include controlling plants from the genera consisting of: Cirsium,
Chamomilla, Echinochloa, Brachiaria.
[0083] An eightieth embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the twentieth embodiment wherein the amount of the mixture is
applied at a rate, expressed in gai/ha or gae/ha of nicosulfuron
selected from the group of rates and ranges of rates consisting of
about: 8.75, 17.5, 35, and from 8.75 to 35, or within any range
defined between any pair of the foregoing values.
[0084] An eighty-first embodiment includes methods according to
either of the twentieth and eightieth embodiments wherein the
controlled plant is at least one plant selected from the group
consisting of: DIGSA, LEFCH, CYPES, ECHOR, CYPRO, and CYPIR, still
other embodiments include controlling plants from the genera
consisting of: Digitaria, Leptochloa, Cyperus, Echinochloa,
Cyperus.
[0085] An eighty-second embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the twenty-first embodiment wherein the amount of the mixture is
applied at a rate, expressed in gai/ha or gae/ha of orthosulfamuron
selected from the group of rates and ranges of rates consisting of
about: 7.5, 15, 30, 60 from 7.5 to 15, from 7.5 to 30, from 7.5 to
60, or within any range defined between any pair of the foregoing
values.
[0086] An eighty-third embodiment includes methods according to
either of the twenty-first and eighty-second embodiments wherein
the controlled plant is at least one plant selected from the group
consisting of: LEFCH, BRAPP, CYPIR, CYPES, ECHOR, SCPMA, still
other embodiments include controlling plants from the genera
consisting of: Leptochloa, Cyperus, Schoenoplectus, Bolboschoenus,
Echinochloa, Brachiaria.
[0087] An eighty-fourth embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the twenty-second embodiment wherein the amount of the mixture is
applied at a rate, expressed in gai/ha or gae/ha of
primisulfuron-methyl selected from the group of rates and ranges of
rates consisting of about: 15, 30 and from 15 to 30, or within any
range defined between any pair of the foregoing values.
[0088] An eighty-fifth embodiment includes methods according to
either of the twenty-second and eighty-fourth embodiments wherein
the controlled plant is at least one plant selected from the group
consisting of: LEFCH, still other embodiments include controlling
plants from the genera consisting of: Leptochloa.
[0089] An eighty-sixth embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the twenty-third embodiment wherein the amount of the mixture is
applied at a rate, expressed in gai/ha or gae/ha of propyrisulfuron
sodium selected from the group of rates and ranges of rates
consisting of about: 11.25, 22.5, 45 and from 11.25 to 45, or
within any range defined between any pair of the foregoing
values.
[0090] An eighty-seventh embodiment includes methods according to
either of the twenty-third and eighty-sixth embodiments wherein the
controlled plant is at least one plant selected from the group
consisting of: BRAPP, SCPMA, FIMMI, still other embodiments include
controlling plants from the genera consisting of: Schoenoplectus,
Bolboschoenus, Brachiaria, Fimbristylis.
[0091] An eighty-eighth embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the twenty-fourth embodiment wherein the amount of the mixture is
applied at a rate, expressed in gai/ha or gae/ha of prosulfuron
selected from the group of rates and ranges of rates consisting of
about: from 7 to 65, from 4.4 to 40, or within any range defined
between any pair of the foregoing values.
[0092] An eighty-ninth embodiment includes methods according to
either of the twenty-fourth and eighty-eighth used in herbicidally
effective rates for controlling the growth of undesirable plants
that have a negative impact on the growth of various crop
plants.
[0093] A ninetieth embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the twenty-fifth embodiment wherein the amount of the mixture is
applied at a rate, expressed in gai/ha or gae/ha of pyrimisulfan
selected from the group of rates and ranges of rates consisting of
about: from 10 to 200, from 15 to 300, or within any range defined
between any pair of the foregoing values.
[0094] A ninety-first embodiment includes methods according to
either of the twenty-fifth and ninetieth used in herbicidally
effective rates for controlling the growth of undesirable plants
that have a negative impact on the growth of various crop
plants.
[0095] A ninety-second embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the twenty-sixth embodiment wherein the amount of the mixture is
applied at a rate, expressed in gai/ha or gae/ha of pyroxasulfone
selected from the group of rates and ranges of rates consisting of
about: from 100 to 1000, from 105 to 350, or within any range
defined between any pair of the foregoing values.
[0096] A ninety-third embodiment includes methods according to
either of the twenty-sixth and ninety-second used in herbicidally
effective rates for controlling the growth of undesirable plants
that have a negative impact on the growth of various crop
plants.
[0097] A ninety-fourth embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the twenty-seventh embodiment wherein the amount of the mixture is
applied at a rate, expressed in gai/ha or gae/ha of rimsulfuron
selected from the group of rates and ranges of rates consisting of
about: 2.19, 4.38, 8.75, and from 2.19 to 8.75, or within any range
defined between any pair of the foregoing values.
[0098] A ninety-fifth embodiment includes methods according to
either of the twenty-seventh and ninety-fourth embodiments wherein
the controlled plant is at least one plant selected from the group
consisting of: IPOHE, CYPES, LEFCH, CYPRO, and DIGSA, still other
embodiments include controlling plants from the genera consisting
of: Ipomoea, Cyperus, Leptochloa, Digitaria.
[0099] A ninety-sixth embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the twenty-eighth embodiment wherein the amount of the mixture is
applied at a rate, expressed in gai/ha or gae/ha of
sulfometuron-methyl selected from the group of rates and ranges of
rates consisting of about: 35, or within any range defined between
any pair of the foregoing values.
[0100] A ninety-seventh embodiment includes methods according to
either of the twenty-eighth and ninety-sixth embodiments wherein
the controlled plant is at least one plant selected from the group
consisting of: DIGSA, still other embodiments include controlling
plants from the genera consisting of: Digitaria.
[0101] A ninety-eighth embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the twenty-ninth embodiment wherein the amount of the mixture is
applied at a rate, expressed in gai/ha or gae/ha of sulfosulfuron
selected from the group of rates and ranges of rates consisting of
about: 8.75 or within any range defined between any pair of the
foregoing values.
[0102] A ninety-ninth embodiment includes methods according to
either of the twenty-ninth and ninety-eighth embodiments wherein
the controlled plant is at least one plant selected from the group
consisting of: LAMPU, VERPE, MATCH, CIRAR, still other embodiments
include controlling plants from the genera consisting of: Lamium,
Veronica, Chamomilla, Cirsium.
[0103] A one-hundredth embodiment includes methods of controlling
undesirable vegetation comprising the step of applying a
herbicidally effective amount of at least one mixture according to
the thirtieth embodiment wherein the amount of the mixture is
applied at a rate, expressed in gai/ha or gae/ha of
thifensulfuron-methyl selected from the group of rates and ranges
of rates consisting of about: 3.75, or within any range defined
between any pair of the foregoing values.
[0104] A one-hundred-first embodiment includes methods according to
either of the thirtieth and one-hundredth embodiments wherein the
controlled plant is at least one plant selected from the group
consisting of: CIRAR, still other embodiments include controlling
plants from the genera consisting of: Cirsium.
[0105] A one-hundred-second embodiment includes methods of
controlling undesirable vegetation comprising the step of applying
a herbicidally effective amount of at least one mixture according
to the thirty-first embodiment wherein the amount of the mixture is
applied at a rate, expressed in gai/ha or gae/ha of triafamone
selected from the group of rates and ranges of rates consisting of
about: from 7 to 200, from 5 to 50, or within any range defined
between any pair of the foregoing values.
[0106] A one-hundred-third embodiment includes methods according to
either of the thirty-first and one-hundred-second used in
herbicidally effective rates for controlling the growth of
undesirable plants that have a negative impact on the growth of
various crop plants.
[0107] A one-hundred-fourth embodiment includes methods of
controlling undesirable vegetation comprising the step of applying
a herbicidally effective amount of at least one mixture according
to the thirty-second embodiment wherein the amount of the mixture
is applied at a rate, expressed in gai/ha or gae/ha of triasulfuron
selected from the group of rates and ranges of rates consisting of
about: from 2.2 to 30, from 5 to 50, or within any range defined
between any pair of the foregoing values.
[0108] A one-hundred-fifth embodiment includes methods according to
either of the thirty-second and one-hundred-fourth used in
herbicidally effective rates for controlling the growth of
undesirable plants that have a negative impact on the growth of
various crop plants.
[0109] A one-hundred-sixth embodiment includes methods of
controlling undesirable vegetation comprising the step of applying
a herbicidally effective amount of at least one mixture according
to the thirty-third embodiment wherein the amount of the mixture is
applied at a rate, expressed in gai/ha or gae/ha of
tribenuron-methyl selected from the group of rates and ranges of
rates consisting of about: 2.2, or within any range defined between
any pair of the foregoing values.
[0110] A one-hundred-eighth embodiment includes methods according
to either of the thirty-third and one-hundred-sixth embodiments
wherein the controlled plant is at least one plant selected from
the group consisting of: MATCH, CIRAR, still other embodiments
include controlling plants from the genera consisting of:
Chamomilla, Cirsium.
[0111] A one-hundred-ninth embodiment includes methods of
controlling undesirable vegetation comprising the step of applying
a herbicidally effective amount of at least one mixture according
to the thirty-fourth embodiment wherein the amount of the mixture
is applied at a rate, expressed in gai/ha or gae/ha of
trifloxysulfuron-sodium selected from the group of rates and ranges
of rates consisting of about: 24, or within any range defined
between any pair of the foregoing values.
[0112] A one-hundred-tenth embodiment includes methods according to
either of the thirty-fourth and one-hundred ninth embodiments
wherein the controlled plant is at least one plant selected from
the group consisting of: DIGSA, still other embodiments include
controlling plants from the genera consisting of: Digitaria.
[0113] Provided herein are herbicidal compositions comprising and
methods for controlling undesirable vegetation utilizing a
herbicidally effective amount of (a) a compound of the formula
(I)
##STR00003##
or an agriculturally acceptable salt or ester thereof, and (b) a
sulfonylurea selected from the group consisting of amidosulfuron,
azimsulfuron, bensulfuron-methyl, chlorsulfuron, cyclosulfamuron,
ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron,
flucetosulfuron, flupyrsulfuron-methyl sodium, foramsulfuron,
imazosulfuron, iofensulfuron, iodosulfuron-methyl sodium,
mesosulfuron-methyl, metsulfuron-methyl, nicosulfuron,
orthosulfamuron, primisulfuron-methyl, propyrisulfuron,
prosulfuron, pyrimisulfan, pyroxasulfone, rimsulfuron,
sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl,
triafamone, triasulfuron, tribenuron-methyl and
trifloxysulfuron-sodium, or an agriculturally acceptable salt or
ester thereof. In certain embodiments, the compositions further
comprise an agriculturally acceptable adjuvant or carrier.
DETAILED DESCRIPTION
Definitions
[0114] As used herein, the compound of formula (I) has the
following structure:
##STR00004##
The compound of formula (I) can be identified by the name
4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-
-carboxylic acid and has been described in U.S. Pat. No. 7,314,849
(B2), which is incorporated herein by reference in its entirety.
Exemplary uses of the compound of the formula (I) include
controlling undesirable vegetation, including grass, broadleaf and
sedge weeds, in multiple non-crop and cropping situations.
[0115] As used herein, amidosulfuron is
N-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-N-methy-
lmethanesulfonamide and possesses the following structure:
##STR00005##
[0116] Its herbicidal activity is exemplified in Tomlin, C., ed. A
World Compendium The Pesticide Manual. 15.sup.th ed. Alton: BCPC
Publications, 2009 (hereafter "The Pesticide Manual, Fifteenth
Edition, 2009."). Amidosulfuron provides, e.g., post-emergence
control of a wide range of broadleaf weeds, e.g., cleavers, in
winter wheat, durum wheat, barley, rye, triticale and oats.
[0117] As used herein, azimsulfuron is
N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-1-methyl-4-(2-methyl-2H--
tetrazol-5-yl)-1H-pyrazole-5-sulfonamide and possesses the
following structure:
##STR00006##
[0118] Its herbicidal activity is exemplified in The Pesticide
Manual, Fifteenth Edition, 2009. Azimsulfuron provides, e.g.,
post-emergence control of annual and perennial broadleaf and sedge
weeds in rice.
[0119] As used herein, bensulfuron-methyl is methyl
2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]methyl]-
benzoate and possesses the following structure:
##STR00007##
[0120] Its herbicidal activity is exemplified in The Pesticide
Manual, Fifteenth Edition, 2009. Bensulfuron-methyl provides, e.g.,
pre- and post-emergence control of annual and perennial broadleaf
weeds and sedges in rice. In certain embodiments, the free
carboxylic acid, with respect to the methyl ester moiety, i.e.,
.alpha.-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-o-toluic
acid, or its salt, is utilized. In certain embodiments, a different
ester, e.g., an alkyl or aralkyl ester is utilized.
[0121] As used herein, chlorsulfuron is
2-chloro-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzen-
esulfonamide and possesses the following structure:
##STR00008##
[0122] Its herbicidal activity is exemplified in The Pesticide
Manual, Fifteenth Edition, 2009. Chlorsulfuron provides control of,
e.g., broadleaf weeds and annual grasses in wheat, barley, oats,
rye, triticale, flax and on non-crop land.
[0123] As used herein, cyclosulfamuron is
N-[[[2-(cyclopropylcarbonyl)phenyl]amino]sulfonyl]-N'-(4,6-dimethoxy-2-py-
rimidinyl)urea and possess the following structure:
##STR00009##
[0124] Its herbicidal activity is exemplified in Senseman, S., ed.
Herbicide Handbook. 9th ed. Lawrence: Weed Science Society of
America, 2007 ("Herbicide Handbook, Ninth Edition, 2007").
Cyclosulfamuron provides control of, e.g., dicotyledonous and sedge
weeds, e.g. Cyperus serotinus, Eleocharis kuroguwai and Sagittaria
pygmaea, in rice and Galium aparine, Matricaria spp., Veronica
spp., Sinapis arvensis and Brassica napus in wheat and barley.
[0125] As used herein, ethametsulfuron-methyl is methyl
2-[[[[[4-ethoxy-6-(methylamino)-1,3,5-triazin-2-yl]amino]carbonyl]amino]s-
ulfonyl]benzoate and possess the following structure:
##STR00010##
Its herbicidal activity is exemplified in the Herbicide Handbook,
Ninth Edition, 2007. Ethametsulfuron-methyl provides, e.g.,
post-emergence control of wild mustard, hempnettle and other
broadleaf weeds in oilseed rape. In some embodiments, the
corresponding carboxylic acid of salt thereof, or a different
ester, e.g., alkyl or aralkyl ester, with respect the methyl ester
moiety, is utilized.
[0126] As used herein, ethoxysulfuron is
2-ethoxyphenyl[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]sulfamate
and possesses the following structure:
##STR00011##
[0127] Its herbicidal activity is exemplified in The Pesticide
Manual, Fifteenth Edition, 2009. Ethoxysulfuron provides, e.g.,
control of broadleaf and sedge weeds in cereals, rice and sugar
cane.
[0128] As used herein, flazasulfuron is
N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(trifluoromethyl)-2-py-
ridinesulfonamide and possess the following structure:
##STR00012##
[0129] Its herbicidal activity is exemplified in the Herbicide
Handbook, Ninth Edition, 2007. Flazasulfuron provides, e.g.,
pre-emergence and postemergence control of grass, broadleaf and
sedge weeds in warm-season turf, vines, sugar cane, citrus, olives
and on railways and other non-crop land.
[0130] As used herein, flucetosulfuron is
1-[3-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-2-py-
ridinyl]-2-fluoropropyl 2-methoxyacetate and possesses the
following structure:
##STR00013##
[0131] Its herbicidal activity is exemplified in The Pesticide
Manual, Fifteenth Edition, 2009. Flucetosulfuron provides control
of, e.g., broadleaf weeds, some grass weeds, and sedges in rice and
cereals.
[0132] As used herein, flupyrsulfuron-methyl sodium is methyl
2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-6-(trif-
luoromethyl)-3-pyridinecarboxylate monosodium salt and possesses
the following structure:
##STR00014##
Its herbicidal activity is exemplified in The Pesticide Manual,
Fifteenth Edition, 2009. Flupyrsulfuron-methyl sodium is used,
e.g., for post-emergent control of grass and broadleaf weeds in
cereals. In certain embodiments, the carboxylic acid or a salt
thereof, or a different ester, e.g., alkyl or aralkyl ester, with
respect to the methyl ester moiety is utilized. In certain
embodiments, a different salt or non-ionic form is utilized.
[0133] As used herein, foramsulfuron is
2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-4-(form-
ylamino)-N,N-dimethylbenzamide and possess the following
structure:
##STR00015##
[0134] Its herbicidal activity is exemplified in the Herbicide
Handbook, Ninth Edition, 2007. Foramsulfuron provides, e.g.,
post-emergence control of grass and broadleaf weeds in maize.
[0135] As used herein, imazosulfuron is
2-chloro-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]imidazo[1,2-a]py-
ridine-3-sulfonamide and possesses the following structure:
##STR00016##
Its herbicidal activity is exemplified in The Pesticide Manual,
Fifteenth Edition, 2009. Imazosulfuron provides, e.g., control of
annual and perennial broadleaf weeds and sedges in paddy rice and
turf.
[0136] As used herein, iodosulfuron-methyl sodium is methyl
4-iodo-2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]-
sulfonyl]benzoate, sodium salt and possesses the following
structure:
##STR00017##
[0137] Its herbicidal activity is exemplified in The Pesticide
Manual, Fifteenth Edition, 2009. Iodosulfuron-methyl sodium
provides, e.g., post-emergence control of grass and broadleaf weeds
in winter, spring and durum wheat, triticale, rye and spring
barley. In certain embodiments, the carboxylic acid or a salt
thereof, or a different ester, e.g., alkyl or aralkyl ester, with
respect to the methyl ester moiety is utilized. In certain
embodiments, a different salt or non-ionic form is utilized.
[0138] As used herein, iofensulfuron is
2-iodo-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenes-
ulfonamide and possesses the following structure:
##STR00018##
[0139] Its herbicidal activity is exemplified in The Pesticide
Manual, Fifteenth Edition, 2009. Iofensulfuron provides control of,
e.g., annual grass, broadleaf and sedge weeds in rice.
[0140] As used herein, mesosulfuron-methyl is methyl
2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-4-[[(me-
thylsulfonyl)amino]methyl]benzoate and possesses the following
structure:
##STR00019##
[0141] Its herbicidal activity is exemplified in The Pesticide
Manual, Fifteenth Edition, 2009. Mesosulfuron-methyl provides,
e.g., early to mid post-emergence control of grass and broadleaf
weeds in winter, spring and durum wheat, triticale and rye. In
certain embodiments, the carboxylic acid or a salt thereof, or a
different ester, e.g., alkyl or aralkyl ester, with respect to the
methyl ester moiety is utilized.
[0142] As used herein, metsulfuron-methyl is methyl
2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfony-
l]benzoate and possesses the following structure:
##STR00020##
[0143] Its herbicidal activity is exemplified in The Pesticide
Manual, Fifteenth Edition, 2009. Metsulfuron-methyl controls, e.g.,
grass and broadleaf weeds in wheat, barley, rice, oats and
triticale. In certain embodiments, the carboxylic acid or a salt
thereof, or a different ester, e.g., alkyl or aralkyl ester, with
respect to the methyl ester moiety is utilized.
[0144] As used herein, nicosulfuron is
2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-N,N-dim-
ethyl-3-pyridinecarboxamide and possesses the following
structure:
##STR00021##
[0145] Its herbicidal activity is exemplified in The Pesticide
Manual, Fifteenth Edition, 2009.
[0146] Nicosulfuron provides, e.g., selective post-emergence
control in maize of annual grass weeds, including Setaria,
Echinochloa, Digitaria, Panicum, Lolium and Avena spp., broadleaf
weeds, including Amaranthus spp. and Cruciferae, and perennials
such as Sorghum halepense and Agropyron repens.
[0147] As used herein, orthosulfamuron is
2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]amino]--
N,N-dimethylbenzamide and possesses the following structure:
##STR00022##
[0148] Its herbicidal activity is exemplified in The Pesticide
Manual, Fifteenth Edition, 2009. Orthosulfamuron provides, e.g.,
early post-emergence control of annual and perennial broadleaf
weeds and sedges in rice, cereals, pastures and sugar cane.
[0149] As used herein, primisulfuron-methyl is methyl
2-[[[[[4,6-bis(difluoromethoxy)-2-pyrimidinyl]amino]carbonyl]amino]sulfon-
yl]benzoate and possesses the following structure:
##STR00023##
[0150] Its herbicidal activity is exemplified in The Pesticide
Manual, Fifteenth Edition, 2009. Primisulfuron-methyl provides,
e.g., post-emergence control of problem grass weeds, including
Sorghum bicolor, Sorghum almum, Sorghum halepense and Agropyron
repens, and many broadleaf weeds, in maize. In certain embodiments,
the carboxylic acid or a salt thereof, or a different ester, e.g.,
alkyl or aralkyl ester, with respect to the methyl ester moiety is
utilized.
[0151] As used herein, propyrisulfuron is
2-chloro-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-6-propylimidazo-
[1,2-b]pyridazine-3-sulfonamide and possesses the following
structure:
##STR00024##
[0152] Its herbicidal activity is exemplified in: Development of a
novel paddy rice herbicide propyrisulfuron (ZETA-ONE), Sumitomo
Kagaku (Osaka, Japan) (2011), (2), 14-25. Publisher: (Sumitomo
Kagaku Kogyo K.K.). Propyrisulfuron is used, e.g., as a rice
herbicide to control annual and perennial paddy weeds, including
Echinochloa spp., sedges and broadleaf weeds.
[0153] As used herein, prosulfuron is
N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]-2-(3,3,3-trifl-
uoropropyl)benzene sulfonamide and possess the following
structure:
##STR00025##
[0154] Its herbicidal activity is exemplified in the Herbicide
Handbook, Ninth Edition, 2007. Prosulfuron provides, e.g.,
post-emergence control of annual broadleaf weeds in maize, sorghum,
cereals, pasture and turf.
[0155] As used herein, pyrimisulfan is
N-[2-[(4,6-dimethoxy-2-pyrimidinyl)hydroxymethyl]-6-(methoxymethyl)phenyl-
]-1,1-difluoromethanesulfonamide and possesses the following
structure:
##STR00026##
[0156] Its herbicidal activity is exemplified in the Journal of
Pesticide Science (Tokyo, Japan) (2012), 37(1), 62-68. Pyrimisulfan
can be used, e.g., as a herbicide for the control of rice weeds in
rice fields.
[0157] As used herein, pyroxasulfone is
3-[[[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]met-
hyl]sulfonyl]-4,5-dihydro-5,5-dimethylisoxazole and possesses the
following structure:
##STR00027##
[0158] Its herbicidal activity is exemplified in The Pesticide
Manual, Fifteenth Edition, 2009. Pyroxasulfone provides, e.g.,
pre-emergence control of annual grasses and some broadleaf weeds in
maize, soya beans, wheat and other crops.
[0159] As used herein, rimsulfuron is
N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(ethylsulfonyl)-2-pyri-
dinesulfonamide and possesses the following structure:
##STR00028##
[0160] Its herbicidal activity is exemplified in The Pesticide
Manual, Fifteenth Edition, 2009. Rimsulfuron provides, e.g.,
post-emergence control of most annual and perennial grasses and
several broadleaf weeds in maize.
[0161] As used herein, sulfometuron-methyl is methyl
2-[[[[(4,6-dimethyl-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]benzoate
and possesses the following structure:
##STR00029##
[0162] Its herbicidal activity is exemplified in The Pesticide
Manual, Fifteenth Edition, 2009. Sulfometuron-methyl provides,
e.g., control of annual and perennial grasses and broadleaf weeds
in non-crop land. It is also used, e.g., for selective weed control
in Bermuda grass and other turf grasses; and in forestry to control
woody tree species in pine trees. In certain embodiments, the
carboxylic acid or a salt thereof, or a different ester, e.g.,
alkyl or aralkyl ester, with respect to the methyl ester moiety is
utilized.
[0163] As used herein, sulfosulfuron is
N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-2-(ethylsulfonyl)imidazo-
[1,2-a]pyridine-3-sulfonamide and possesses the following
structure:
##STR00030##
[0164] Its herbicidal activity is exemplified in The Pesticide
Manual, Fifteenth Edition, 2009. Sulfosulfuron can be used, e.g.,
in the control of annual broadleaf weeds and grass weeds in
cereals.
[0165] As used herein, thifensulfuron-methyl is methyl
3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfony-
l]-2-thiophenecarboxylate and possesses the following
structure:
##STR00031##
[0166] Its herbicidal activity is exemplified in The Pesticide
Manual, Fifteenth Edition, 2009. Thifensulfuron-methyl is used,
e.g., in the control of annual weeds in cereals, maize and pasture.
In certain embodiments, the carboxylic acid or a salt thereof, or a
different ester, e.g., alkyl or aralkyl ester, with respect to the
methyl ester moiety is utilized.
[0167] As used herein, triafamone is
N-[2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-1,1-dif-
luoro-N-methylmethanesulfonamide and possesses the following
structure:
##STR00032##
[0168] Its herbicidal activity is exemplified in the published
article Shijie Nongyao (2011), 33(3), 22-24. Triafamone is used,
e.g., in the pre- and post-emergence control of grass, broadleaf
and sedge weeds in rice.
[0169] As used herein, triasulfuron is
2-(2-chloroethoxy)-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbo-
nyl]benzenesulfonamide and possess the following structure:
##STR00033##
[0170] Its herbicidal activity is exemplified in the Herbicide
Handbook, Ninth Edition, 2007. Triasulfuron is used, e.g., in the
pre- and post-emergence control of broadleaf weeds in wheat, barley
and triticale.
[0171] As used herein, tribenuron-methyl is methyl
2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)methylamino]carbonyl]amino]s-
ulfonyl]benzoate and possesses the following structure:
##STR00034##
[0172] Its herbicidal activity is exemplified in The Pesticide
Manual, Fifteenth Edition, 2009. Tribenuron-methyl is used, e.g.,
in post-emergence control of broadleaf weeds in cereal crops,
including wheat, barley, oats, rye and triticale.
[0173] As used herein, trifloxysulfuron-sodium is
N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(2,2,2-trifluoroethoxy-
)-2-pyridinesulfonamide, sodium salt and possesses the following
structure:
##STR00035##
[0174] Its herbicidal activity is exemplified in The Pesticide
Manual, Fifteenth Edition, 2009. Trifloxysulfuron-sodium is used
for post-emergence grass, sedge and broadleaf weed control in
cotton and sugar cane. It is also used in turf and weed control in
plantations. In certain embodiments, a different salt or non-ionic
form is utilized.
[0175] As used herein, herbicide means a compound, e.g., active
ingredient that kills, controls or otherwise adversely modifies the
growth of plants.
[0176] As used herein, a herbicidally effective or vegetation
controlling amount is an amount of active ingredient which causes
an adversely modifying effect to the vegetation e.g., causing
deviations from natural development, killing, effecting regulation,
causing desiccation, causing retardation, and the like.
[0177] As used herein, controlling undesirable vegetation means
preventing, reducing, killing, or otherwise adversely modifying the
development of plants and vegetation. Described herein are methods
of controlling undesirable vegetation through the application of
certain herbicide combinations or compositions. Methods of
application include, but are not limited to applications to the
vegetation or locus thereof, e.g., application to the area adjacent
to the vegetation, as well as preemergence, postemergence, foliar
(broadcast, directed, banded, spot, mechanical, over-the-top, or
rescue), and in-water applications (emerged and submerged
vegetation, broadcast, spot, mechanical, water-injected, granular
broadcast, granular spot, shaker bottle, or stream spray) via hand,
backpack, machine, tractor, or aerial (airplane and helicopter)
application methods.
[0178] As used herein, plants and vegetation include, but are not
limited to, germinant seeds, emerging seedlings, plants emerging
from vegetative propagules, immature vegetation, and established
vegetation.
[0179] As used herein, agriculturally acceptable salts and esters
refer to salts and esters that exhibit herbicidal activity, or that
are or can be converted in plants, water, or soil to the referenced
herbicide. Exemplary agriculturally acceptable esters are those
that are or can be hydrolyzed, oxidized, metabolized, or otherwise
converted, e.g., in plants, water, or soil, to the corresponding
carboxylic acid which, depending on the pH, may be in the
dissociated or undissociated form.
[0180] Exemplary salts include those derived from alkali or
alkaline earth metals and those derived from ammonia and amines.
Exemplary cations include sodium, potassium, magnesium, and aminium
cations of the formula:
R.sup.1R.sup.2R.sup.3R.sup.4N.sup.+
wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each, independently
represents hydrogen or C.sub.1-C.sub.12 alkyl, C.sub.3-C.sub.12
alkenyl or C.sub.3-C.sub.12 alkynyl, each of which is optionally
substituted by one or more hydroxy, C.sub.1-C.sub.4 alkoxy,
C.sub.1-C.sub.4 alkylthio or phenyl groups, provided that R.sup.1,
R.sup.2, R.sup.3 and R.sup.4 are sterically compatible.
Additionally, any two of R.sup.1, R.sup.2, R.sup.3 and R.sup.4
together may represent an aliphatic difunctional moiety containing
one to twelve carbon atoms and up to two oxygen or sulfur atoms.
Salts can be prepared by treatment with a metal hydroxide, such as
sodium hydroxide, with an amine, such as ammonia, trimethylamine,
diethanolamine, 2-methylthiopropylamine, bisallylamine,
2-butoxyethylamine, morpholine, cyclododecylamine, or benzylamine
or with a tetraalkylammonium hydroxide, such as tetramethylammonium
hydroxide or choline hydroxide.
[0181] Exemplary esters include those derived from C.sub.1-C.sub.12
alkyl, C.sub.3-C.sub.12 alkenyl, C.sub.3-C.sub.12 alkynyl or
C.sub.7-C.sub.10 aryl-substituted alkyl alcohols, such as methyl
alcohol, isopropyl alcohol, 1-butanol, 2-ethylhexanol,
butoxyethanol, methoxypropanol, allyl alcohol, propargyl alcohol,
cyclohexanol or unsubstituted or substituted benzyl alcohols.
Benzyl alcohols may be substituted with from 1-3 substituents
independently selected from halogen, C.sub.1-C.sub.4 alkyl or
C.sub.1-C.sub.4 alkoxy. Esters can be prepared by coupling of the
acids with the alcohol using any number of suitable activating
agents such as those used for peptide couplings such as
dicyclohexylcarbodiimide (DCC) or carbonyl diimidazole (CDI); by
reacting the acids with alkylating agents such as alkylhalides or
alkylsulfonates in the presence of a base such as triethylamine or
lithium carbonate; by reacting the corresponding acid chloride of
an acid with an appropriate alcohol; by reacting the corresponding
acid with an appropriate alcohol in the presence of an acid
catalyst or by transesterification.
Compositions and Methods
[0182] Provided herein are herbicidal compositions comprising an
herbicidally effective amount of (a) a compound of the formula
(I)
##STR00036##
or an agriculturally acceptable salt or ester thereof, and (b) a
sulfonylurea selected from the group consisting of amidosulfuron,
azimsulfuron, bensulfuron-methyl, chlorsulfuron, cyclosulfamuron,
ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron,
flucetosulfuron, flupyrsulfuron-methyl sodium, foramsulfuron,
imazosulfuron, iofensulfuron, iodosulfuron-methyl sodium,
mesosulfuron-methyl, metsulfuron-methyl, nicosulfuron,
orthosulfamuron, primisulfuron-methyl, propyrisulfuron,
prosulfuron, pyrimisulfan, pyroxasulfone, rimsulfuron,
sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl,
triafamone, triasulfuron, tribenuron-methyl and
trifloxysulfuron-sodium or an agriculturally acceptable salt or
ester thereof.
[0183] Provided herein are also methods of controlling undesirable
vegetation comprising contacting the vegetation or the locus
thereof, i.e., area adjacent to the vegetation, with or applying to
the soil or water to prevent the emergence or growth of vegetation
a herbicidally effective amount of the compound of formula (I) or
agriculturally acceptable salt or ester thereof and (b) a
sulfonylurea selected from the group consisting of: amidosulfuron,
azimsulfuron, bensulfuron-methyl, chlorsulfuron, cyclosulfamuron,
ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron,
flucetosulfuron, flupyrsulfuron-methyl sodium, foramsulfuron,
imazosulfuron, iofensulfuron, iodosulfuron-methyl sodium,
mesosulfuron-methyl, metsulfuron-methyl, nicosulfuron,
orthosulfamuron, primisulfuron-methyl, propyrisulfuron,
prosulfuron, pyrimisulfan, pyroxasulfone, rimsulfuron,
sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl,
triafamone, triasulfuron, tribenuron-methyl and
trifloxysulfuron-sodium or an agriculturally acceptable salt or
ester thereof.
[0184] In certain embodiments, the methods employ the compositions
described herein.
[0185] Furthermore, in some embodiments, the combination of
compound (I) or agriculturally acceptable salt or ester thereof and
sulfonylurea, or an agriculturally acceptable salt or ester thereof
exhibits synergism, e.g., the herbicidal active ingredients are
more effective in combination than when applied individually.
Synergism has been defined as "an interaction of two or more
factors such that the effect when combined is greater than the
predicted effect based on the response of each factor applied
separately." Senseman, S., ed. Herbicide Handbook. 9.sup.th ed.
Lawrence: Weed Science Society of America, 2007 In certain
embodiments, the compositions exhibit synergy as determined by the
Colby's equation. Colby, S. R. 1967. Calculation of the synergistic
and antagonistic response of herbicide combinations. Weeds
15:20-22.
[0186] In certain embodiments of the compositions and methods
described herein, the compound of formula (I), i.e., the carboxylic
acid, is employed. In certain embodiments, a carboxylate salt of
the compound of formula (I) is employed. In certain embodiments, an
aralkyl or alkyl ester is employed. In certain embodiments, a
benzyl, substituted benzyl, or C.sub.1-4 alkyl, e.g., n-butyl ester
is employed. In certain embodiments, the benzyl ester is
employed.
[0187] In some embodiments, the compound of formula (I) or salt or
ester thereof and sulfonylurea are formulated in one composition,
tank mixed, applied simultaneously, or applied sequentially.
[0188] Herbicidal activity is exhibited by the compounds when they
are applied directly to the plant or to the locus of the plant,
i.e. area adjacent to the plant, at any stage of growth. The effect
observed depends upon the plant species to be controlled, the stage
of growth of the plant, the application parameters of dilution and
spray drop size, the particle size of solid components, the
environmental conditions at the time of use, the specific compound
employed, the specific adjuvants and carriers employed, the soil
type, and the like, as well as the amount of chemical applied.
These and other factors can be adjusted to promote non-selective or
selective herbicidal action. In some embodiments, the compositions
described herein are applied as a post-emergence application,
pre-emergence application, or in-water application to flooded paddy
rice or water bodies (e.g., ponds, lakes and streams), to
relatively immature undesirable vegetation to achieve the maximum
control of weeds.
[0189] In some embodiments, the compositions and methods provided
herein are utilized to control weeds in crops, including but not
limited to direct-seeded, water-seeded and transplanted rice,
cereals, wheat, barley, oats, rye, sorghum, corn/maize, sugarcane,
sunflower, oilseed rape, canola, sugar beet, soybean, cotton,
pineapple, pastures, grasslands, rangelands, fallowland, turf, tree
and vine orchards, aquatics, plantation crops, vegetables,
industrial vegetation management (IVM) and rights-of-way (ROW).
[0190] In certain embodiments, the compositions and methods
provided herein are utilized to control weeds in rice. In certain
embodiments, the rice is direct-seeded, water-seeded, or
transplanted rice.
[0191] The compositions and methods described herein may be used to
control undesirable vegetation in glyphosate-tolerant-,
5-enolpyruvylshikimate-3-phosphate (EPSP) synthase
inhibitor-tolerant-, glufosinate-tolerant-, glutamine synthetase
inhibitor-tolerant-, dicamba-tolerant-, phenoxy auxin-tolerant-,
pyridyloxy auxin-tolerant-, auxin-tolerant-, auxin transport
inhibitor-tolerant-, aryloxyphenoxypropionate-tolerant-,
cyclohexanedione-tolerant-, phenylpyrazoline-tolerant-, acetyl CoA
carboxylase (ACCase) inhibitor-tolerant-, imidazolinone-tolerant-,
sulfonylurea-tolerant-, pyrimidinylthiobenzoate-tolerant-,
triazolopyrimidine-tolerant-,
sulfonylaminocarbonyltriazolinone-tolerant-, acetolactate synthase
(ALS) or acetohydroxy acid synthase (AHAS) inhibitor-tolerant-,
4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-tolerant-,
phytoene desaturase inhibitor-tolerant-, carotenoid biosynthesis
inhibitor-tolerant-, protoporphyrinogen oxidase (PPO)
inhibitor-tolerant-, cellulose biosynthesis inhibitor-tolerant-,
mitosis inhibitor-tolerant-, microtubule inhibitor-tolerant-, very
long chain fatty acid inhibitor-tolerant-, fatty acid and lipid
biosynthesis inhibitor-tolerant-, photosystem I
inhibitor-tolerant-, photosystem II inhibitor-tolerant-,
triazine-tolerant-, and bromoxynil-tolerant-crops (such as, but not
limited to, soybean, cotton, canola/oilseed rape, rice, cereals,
corn, sorghum, sunflower, sugar beet, sugarcane, turf, etc.), for
example, in conjunction with glyphosate, EPSP synthase inhibitors,
glufosinate, glutamine synthase inhibitors, dicamba, phenoxy
auxins, pyridyloxy auxins, synthetic auxins, auxin transport
inhibitors, aryloxyphenoxypropionates, cyclohexanediones,
phenylpyrazolines, ACCase inhibitors, imidazolinones,
sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines,
sulfonylaminocarbonyltriazolinones, ALS or AHAS inhibitors, HPPD
inhibitors, phytoene desaturase inhibitors, carotenoid biosynthesis
inhibitors, PPO inhibitors, cellulose biosynthesis inhibitors,
mitosis inhibitors, microtubule inhibitors, very long chain fatty
acid inhibitors, fatty acid and lipid biosynthesis inhibitors,
photosystem I inhibitors, photosystem II inhibitors, triazines, and
bromoxynil. The compositions and methods may be used in controlling
undesirable vegetation in crops possessing multiple or stacked
traits conferring tolerance to multiple chemistries and/or
inhibitors of multiple modes of action. In some embodiments, the
compound of formula (I) or salt or ester thereof and complementary
herbicide or salt or ester thereof are used in combination with
herbicides that are selective for the crop being treated and which
complement the spectrum of weeds controlled by these compounds at
the application rate employed. In some embodiments, the
compositions described herein and other complementary herbicides
are applied at the same time, either as a combination formulation,
as a tank mix, or sequentially.
[0192] The compositions and methods may be used in controlling
undesirable vegetation in crops possessing agronomic stress
tolerance (including but not limited to drought, cold, heat, salt,
water, nutrient, fertility, pH), pest tolerance (including but not
limited to insects, fungi and pathogens) and crop improvement
traits (including but not limited to yield; protein, carbohydrate,
or oil content; protein, carbohydrate, or oil composition; plant
stature and plant architecture).
[0193] The compositions and methods provided herein are utilized to
control undesirable vegetation. Undesirable vegetation includes,
but is not limited to, undesirable vegetation that occurs in
direct-seeded, water-seeded, and transplanted rice, cereals, wheat,
barley, oats, rye, sorghum, corn/maize, sugarcane, sunflower,
oilseed rape, canola, sugar beet, soybean, cotton, pineapple,
pastures, grasslands, rangelands, fallowland, turf, tree and vine
orchards, ornamental species, aquatics, plantation crops,
vegetables, industrial vegetation management (IVM) and
rights-of-way (ROW).
[0194] In some embodiments, the methods provided herein are
utilized to control undesirable vegetation in rice. In certain
embodiments, the undesirable vegetation is Brachiaria platyphylla
(Groseb.) Nash or Urochloa platyphylla (Nash) R. D. Webster
(broadleaf signalgrass, BRAPP), Digitaria sanguinalis (L.) Scop.
(large crabgrass, DIGSA), Echinochloa species (ECHSS), Echinochloa
crus-galli (L.) P. Beauv. (barnyardgrass, ECHCG), Echinochloa
crus-pavonis (Kunth) Schult. (gulf cockspur, ECHCV), Echinochloa
colonum (L.) LINK (junglerice, ECHCO), Echinochloa oryzoides (Ard.)
Fritsch (early watergrass, ECHOR), Echinochloa oryzicola (Vasinger)
Vasinger (late watergrass, ECHPH), Echinochloa phyllopogon (Stapf)
Koso-Pol. (rice barnyardgrass, ECHPH), Echinochloa polystachya
(Kunth) Hitchc. (creeping river grass, ECHPO), Ischaemum rugosum
Salisb. (saramollagrass, ISCRU), Leptochloa chinensis (L.) Nees
(Chinese sprangletop, LEFCH), Leptochloa fascicularis (Lam.) Gray
(bearded sprangletop, LEFFA), Leptochloa panicoides (Presl.)
Hitchc. (Amazon sprangletop, LEFPA), Oryza species (red and weedy
rice, ORYSS), Panicum dichotomiflorum (L.) Michx. (fall panicum,
PANDI), Paspalum dilatatum Poir. (dallisgrass, PASDI), Rottboellia
cochinchinensis (Lour.) W. D. Clayton (itchgrass, ROOEX), Cyperus
species (CYPSS), Cyperus difformis L. (smallflower flatsedge,
CYPDI), Cyperus dubius Rottb. (MAPDU), Cyperus esculentus L.
(yellow nutsedge, CYPES), Cyperus iria L. (rice flatsedge, CYPIR),
Cyperus rotundus L. (purple nutsedge, CYPRO), Cyperus serotinus
Rottb./C. B. Clarke (tidalmarsh flatsedge, CYPSE), Eleocharis
species (ELOSS), Fimbristylis miliacea (L.) Vahl (globe fringerush,
FIMMI), Schoenoplectus species (SCPSS), Schoenoplectus juncoides
Roxb. (Japanese bulrush, SCPJU), Bolboschoenus maritimus (L.) Palla
or Schoenoplectus maritimus L. Lye (sea clubrush, SCPMA),
Schoenoplectus mucronatus L. (ricefield bulrush, SCPMU),
Aeschynomene species, (jointvetch, AESSS), Alternanthera
philoxeroides (Mart.) Griseb. (alligatorweed, ALRPH), Alisma
plantago-aquatica L. (common waterplantain, ALSPA), Amaranthus
species, (pigweeds and amaranths, AMASS), Ammannia coccinea Rottb.
(redstem, AMMCO), Commelina benghalensis L. (Benghal dayflower,
COMBE), Eclipta alba (L.) Hassk. (American false daisy, ECLAL),
Heteranthera limosa (SW.) Willd./Vahl (ducksalad, HETLI),
Heteranthera reniformis R. & P. (roundleaf mudplantain, HETRE),
Ipomoea species (morningglories, IPOSS), Ipomoea hederacea (L.)
Jacq. (ivyleaf morningglory, IPOHE), Lindernia dubia (L.) Pennell
(low false pimpernel, LIDDU), Ludwigia species (LUDSS), Ludwigia
linifolia Poir. (southeastern primrose-willow, LUDLI), Ludwigia
octovalvis (Jacq.) Raven (longfruited primrose-willow, LUDOC),
Monochoria korsakowii Regel & Maack (monochoria, MOOKA),
Monochoria vaginalis (Burm. F.) C. Presl ex Kuhth, (monochoria,
MOOVA), Murdannia nudiflora (L.) Brenan (doveweed, MUDNU),
Polygonum pensylvanicum L., (Pennsylvania smartweed, POLPY),
Polygonum persicaria L. (ladysthumb, POLPE), Polygonum
hydropiperoides Michx. (POLHP, mild smartweed), Rotala indica
(Willd.) Koehne (Indian toothcup, ROTIN), Sagittaria species,
(arrowhead, SAGSS), Sesbania exaltata (Raf.) Cory/Rydb. Ex Hill
(hemp sesbania, SEBEX), or Sphenoclea zeylanica Gaertn. (gooseweed,
SPDZE).
[0195] In some embodiments, the methods provided herein are
utilized to control undesirable vegetation in cereals. In certain
embodiments, the undesirable vegetation is Alopecurus myosuroides
Huds. (blackgrass, ALOMY), Apera spica-venti (L.) Beauv.
(windgrass, APESV), Avena fatua L. (wild oat, AVEFA), Bromus
tectorum L. (downy brome, BROTE), Lolium multiflorum Lam. (Italian
ryegrass, LOLMU), Phalaris minor Retz. (littleseed canarygrass,
PHAMI), Poa annua L. (annual bluegrass, POANN), Setaria pumila
(Poir.) Roemer & J. A. Schultes (yellow foxtail, SETLU),
Setaria viridis (L.) Beauv. (green foxtail, SETVI), Amaranthus
retroflexus L. (redroot pigweed, AMARE), Brassica species (BRSSS),
Chenopodium album L. (common lambsquarters, CHEAL), Cirsium arvense
(L.) Scop. (Canada thistle, CIRAR), Galium aparine L. (catchweed
bedstraw, GALAP), Kochia scoparia (L.) Schrad. (kochia, KCHSC),
Lamium purpureum L. (purple deadnettle, LAMPU), Matricaria recutita
L. (wild chamomile, MATCH), Matricaria matricarioides (Less.)
Porter (pineappleweed, MATMT), Papaver rhoeas L. (common poppy,
PAPRH), Polygonum convolvulus L. (wild buckwheat, POLCO), Salsola
tragus L. (Russian thistle, SASKR), Sinapis species (SINSS),
Sinapis arvensis L. (wild mustard, SINAR), Stellaria media (L.)
Vill. (common chickweed, STEME), Veronica persica Poir. (Persian
speedwell, VERPE), Viola arvensis Murr. (field violet, VIOAR), or
Viola tricolor L. (wild violet, VIOTR).
[0196] In some embodiments, the methods provided herein are
utilized to control undesirable vegetation in range and pasture,
fallowland, IVM and ROW. In certain embodiments, the undesirable
vegetation is Ambrosia artemisiifolia L. (common ragweed, AMBEL),
Cassia obtusifolia (sickle pod, CASOB), Centaurea maculosa auct.
non Lam. (spotted knapweed, CENMA), Cirsium arvense (L.) Scop.
(Canada thistle, CIRAR), Convolvulus arvensis L. (field bindweed,
CONAR), Daucus carota L. (wild carrot, DAUCA), Euphorbia esula L.
(leafy spurge, EPHES), Lactuca serriola L./Torn. (prickly lettuce,
LACSE), Plantago lanceolata L. (buckhorn plantain, PLALA), Rumex
obtusifolius L. (broadleaf dock, RUMOB), Sida spinosa L. (prickly
sida, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Sonchus
arvensis L. (perennial sowthistle, SONAR), Solidago species
(goldenrod, SOOSS), Taraxacum officinale G. H. Weber ex Wiggers
(dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or
Urtica dioica L. (common nettle, URTDI).
[0197] In some embodiments, the methods provided herein are
utilized to control undesirable vegetation found in row crops, tree
and vine crops, and perennial crops. In certain embodiments, the
undesirable vegetation is Alopecurus myosuroides Huds. (blackgrass,
ALOMY), Avena fatua L. (wild oat, AVEFA), Brachiaria decumbens
Stapf. or Urochloa decumbens (Stapf) R. D. Webster (Surinam grass,
BRADC), Brachiaria brizantha (Hochst. ex A. Rich.) Stapf. or
Urochloa brizantha (Hochst. ex A. Rich.) R. D. (beard grass,
BRABR), Brachiaria platyphylla (Groseb.) Nash or Urochloa
platyphylla (Nash) R. D. Webster (broadleaf signalgrass, BRAPP),
Brachiaria plantaginea (Link) Hitchc. or Urochloa plantaginea
(Link) R. D. Webster (alexandergrass, BRAPL), Cenchrus echinatus L.
(southern sandbar, CENEC), Digitaria horizontalis Willd. (Jamaican
crabgrass, DIGHO), Digitaria insularis (L.) Mez ex Ekman
(sourgrass, TRCIN), Digitaria sanguinalis (L.) Scop. (large
crabgrass, DIGSA), Echinochloa crus-galli (L.) P. Beauv.
(barnyardgrass, ECHCG), Echinochloa colonum (L.) Link (junglerice,
ECHCO), Eleusine indica (L.) Gaertn. (goosegrass, ELEIN), Lolium
multiflorum Lam. (Italian ryegrass, LOLMU), Panicum dichotomiflorum
Michx. (fall panicum, PANDI), Panicum miliaceum L. (wild-proso
millet, PANMI), Setaria faberi Herrm. (giant foxtail, SETFA),
Setaria viridis (L.) Beauv. (green foxtail, SETVI), Sorghum
halepense (L.) Pers. (Johnsongrass, SORHA), Sorghum bicolor (L.)
Moench ssp. Arundinaceum (shattercane, SORVU), Cyperus esculentus
L. (yellow nutsedge, CYPES), Cyperus rotundus L. (purple nutsedge,
CYPRO), Abutilon theophrasti Medik. (velvetleaf, ABUTH), Amaranthus
species (pigweeds and amaranths, AMASS), Ambrosia artemisiifolia L.
(common ragweed, AMBEL), Ambrosia psilostachya DC. (western
ragweed, AMBPS), Ambrosia trifida L. (giant ragweed, AMBTR), Anoda
cristata (L.) Schlecht. (spurred anoda, ANVCR), Asclepias syriaca
L. (common milkweed, ASCSY), Bidens pilosa L. (hairy beggarticks,
BIDPI), Borreria species (BOISS), Borreria alata (Aubl.) DC. or
Spermacoce alata Aubl. (broadleaf buttonweed, BOILF), Spermacose
latifolia (broadleaved button weed, BOILF), Chenopodium album L.
(common lambsquarters, CHEAL), Cirsium arvense (L.) Scop. (Canada
thistle, CIRAR), Commelina benghalensis L. (tropical spiderwort,
COMBE), Datura stramonium L. (jimsonweed, DATST), Daucus carota L.
(wild carrot, DAUCA), Euphorbia heterophylla L. (wild poinsettia,
EPHHL), Euphorbia hirta L. or Chamaesyce hirta (L.) Millsp. (garden
spurge, EPHHI), Euphorbia dentata Michx. (toothed spurge, EPHDE),
Erigeron bonariensis L. or Conyza bonariensis (L.) Cronq. (hairy
fleabane, ERIBO), Erigeron canadensis L. or Conyza canadensis (L.)
Cronq. (Canadian fleabane, ERICA), Conyza sumatrensis (Retz.) E. H.
Walker (tall fleabane, ERIFL), Helianthus annuus L. (common
sunflower, HELAN), Jacquemontia tamnifolia (L.) Griseb.
(smallflower morningglory, IAQTA), Ipomoea hederacea (L.) Jacq.
(ivyleaf morningglory, IPOHE), Ipomoea lacunosa L. (white
morningglory, IPOLA), Lactuca serriola L./Torn. (prickly lettuce,
LACSE), Portulaca oleracea L. (common purslane, POROL), Richardia
species (pusley, RCHSS), Sida species (sida, SIDSS), Sida spinosa
L. (prickly sida, SIDSP), Sinapis arvensis L. (wild mustard,
SINAR), Solanum ptychanthum Dunal (eastern black nightshade,
SOLPT), Tridax procumbens L. (coat buttons, TRQPR), or Xanthium
strumarium L. (common cocklebur, XANST).
[0198] In some embodiments, the methods provided herein are
utilized to control undesirable vegetation in turf. In certain
embodiments, the undesirable vegetation is Bellis perennis L.
(English daisy, BELPE), Cyperus esculentus L. (yellow nutsedge,
CYPES), Cyperus species (CYPSS), Digitaria sanguinalis (L.) Scop.
(large crabgrass, DIGSA), Diodia virginiana L. (Virginia
buttonweed, DIQVI), Euphorbia species (spurge, EPHSS), Glechoma
hederacea L. (ground ivy, GLEHE), Hydrocotyle umbellata L.
(dollarweed, HYDUM), Kyllinga species (kylling a, KYLSS), Lamium
amplexicaule L. (henbit, LAMAM), Murdannia nudiflora (L.) Brenan
(doveweed, MUDNU), Oxalis species (woodsorrel, OXASS), Plantago
major L. (broadleaf plantain, PLAMA), Plantago lanceolata L.
(buckhorn/narrowleaf plantain, PLALA), Phyllanthus urinaria L.
(chamberbitter, PYLTE), Rumex obtusifolius L. (broadleaf dock,
RUMOB), Stachys floridana Shuttlew. (Florida betony, STAFL),
Stellaria media (L.) Vill. (common chickweed, STEME), Taraxacum
officinale G. H. Weber ex Wiggers (dandelion, TAROF), Trifolium
repens L. (white clover, TRFRE), or Viola species (wild violet,
VIOSS).
[0199] In some embodiments, the compositions and methods provided
herein are utilized to control undesirable vegetation consisting of
grass, broadleaf and sedge weeds. In certain embodiments, the
compositions and methods provided herein are utilized to control
undesirable vegetation including, but not limited to Brachiaria or
Urochloa, Bolboschoenus, Cassia, Chamomilla, Cirsium, Cyperus,
Digitaria, Echinochloa, Fimbristylis, Galium, Ipomoea, Ischaemum,
Lamium, Leptochloa, Portulaca, Schoenoplectus, Sida, Veronica and
Viola.
[0200] In certain embodiments, the combination of compound (I) or
agriculturally acceptable ester or salt thereof and sulfonylurea or
agriculturally acceptable salt or ester thereof is used to control
Brachiaria platyphylla (Griseb.) Nash or Urochloa platyphylla
(Nash) R. D. Webster (broadleaf signalgrass, BRAPP), Cassia
obtusifolia L. (sicklepod, CASOB), Chamomilla chamomilla (L.) Rydb.
(scented mayweed, MATCH), Cirsium arvense (L.) Scop. (Canada
thistle, CIRAR), Cyperus difformis L. (smallflower umbrella sedge,
CYPDI), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus
iria L. (rice flatsedge, CYPIR), Cyperus rotundus L. (purple
nutsedge, CYPRO), Digitaria sanguinalis (L.) Scop. (large
crabgrass, DIGSA), Echinochloa crus-galli (L.) Beauv.
(barnyardgrass, ECHCG), Echinochloa colona (L.) Link (junglerice,
ECHCO), Echinochloa oryzoides (Ard.) Fritsch (early watergrass,
ECHOR), Fimbristylis miliacea (L.) Vahl (globe fringerush, FIMMI),
Galium aparine (L.) (cleavers, GALAP), Ipomoea hederacea Jacq.
(ivyleaf morningglory, IPOHE), Ischaemum rugosum Salisb.
(saramollagrass, ISCRU), Lamium purpureum (L.) (purple deadnettle,
LAMPU), Leptochloa chinensis (L.) Nees (Chinese sprangletop,
LEFCH), Portulaca oleracea L. (portulaca, POROL), Schoenoplectus
juncoides (Roxb.) Palla (Japanese bulrush, SCPJU), Bolboschoenus
maritimus (L.) Palla or Schoenoplectus maritimus (L.) Lye (sea
clubrush, SCPMA), Sida spinosa L. (sida, prickly, SIDSP), Veronica
persica Poir. (bird's-eye speedwell, VERPE) and Viola tricolor (L.)
(wild pansy, VIOTR).
[0201] The compounds of formula I or agriculturally acceptable salt
or ester thereof may be used to control herbicide resistant or
tolerant weeds. The methods employing the combination of a compound
of formula I or agriculturally acceptable salt or ester thereof and
the compositions described herein may also be employed to control
herbicide resistant or tolerant weeds. Exemplary resistant or
tolerant weeds include, but are not limited to, biotypes resistant
or tolerant to acetolactate synthase (ALS) or acetohydroxy acid
synthase (AHAS) inhibitors (e.g., imidazolinones, sulfonylureas,
pyrimidinylthiobenzoates, triazolopyrimidines,
sulfonylaminocarbonyltriazolinones), photosystem II inhibitors
(e.g., phenylcarbamates, pyridazinones, triazines, triazinones,
uracils, amides, ureas, benzothiadiazinones, nitriles,
phenylpyridazines), acetyl CoA carboxylase (ACCase) inhibitors
(e.g., aryloxyphenoxypropionates, cyclohexanediones,
phenylpyrazolines), synthetic auxins (e.g., benzoic acids,
phenoxycarboxylic acids, pyridine carboxylic acids, quinoline
carboxylic acids), auxin transport inhibitors (e.g., phthalamates,
semicarbazones), photosystem I inhibitors (e.g., bipyridyliums),
5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors
(e.g., glyphosate), glutamine synthetase inhibitors (e.g.,
glufosinate, bialafos), microtubule assembly inhibitors, (e.g.,
benzamides, benzoic acids, dinitroanilines, phosphoramidates,
pyridines), mitosis inhibitors (e.g., carbamates), very long chain
fatty acid (VLCFA) inhibitors (e.g., acetamides, chloroacetamides,
oxyacetamides, tetrazolinones), fatty acid and lipid synthesis
inhibitors (e.g., phosphorodithioates, thiocarbamates,
benzofuranes, chlorocarbonic acids), protoporphyrinogen oxidase
(PPO) inhibitors (e.g., diphenylethers, N-phenylphthalimides,
oxadiazoles, oxazolidinediones, phenylpyrazoles, pyrimidindiones,
thiadiazoles, triazolinones), carotenoid biosynthesis inhibitors
(e.g., clomazone, amitrole, aclonifen), phytoene desaturase (PDS)
inhibitors (e.g., amides, anilidex, furanones, phenoxybutan-amides,
pyridiazinones, pyridines), 4-hydroxyphenyl-pyruvate-dioxygenase
(HPPD) inhibitors (e.g., callistemones, isoxazoles, pyrazoles,
triketones), cellulose biosynthesis inhibitors (e.g., nitriles,
benzamides, quinclorac, triazolocarboxamides), herbicides with
multiple modes-of-action such as quinclorac, and unclassified
herbicides such as arylaminopropionic acids, difenzoquat,
endothall, and organoarsenicals. Exemplary resistant or tolerant
weeds include, but are not limited to, biotypes with resistance or
tolerance to multiple herbicides, biotypes with resistance or
tolerance to multiple chemical classes, biotypes with resistance or
tolerance to multiple herbicide modes-of-action, and biotypes with
multiple resistance or tolerance mechanisms (e.g., target site
resistance or metabolic resistance).
[0202] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with amidosulfuron or salt thereof.
With respect to the compositions, in some embodiments of the
compositions described herein, the weight ratio of the compound of
formula (I) or salt or ester thereof to amidosulfuron or salt
thereof is within the range of from about 1:20 to about 34:1. In
certain embodiments, the weight ratio of the compound of formula
(I) or salt or ester thereof to amidosulfuron or salt thereof is
within the range of from about 1:5 to about 8:1. In certain
embodiments, the weight ratio of the compound of formula (I) or
salt or ester thereof to amidosulfuron or salt thereof is within
the range of from about 0.25:1 to about 4:1. In certain
embodiments, the weight ratio of the compound of formula (I) or
salt or ester thereof to amidosulfuron or salt thereof is within
the range of from about 0.50:1 to about 2:1. In certain
embodiments, the weight ratio of the compound of formula (I) or
salt or ester thereof to amidosulfuron or salt thereof is about
1:1.1. In certain embodiments, the compositions provided herein
comprise the benzyl ester of the compound of formula (I) and
amidosulfuron. In one embodiment, the composition comprises the
benzyl ester of the compound of formula (I) and amidosulfuron,
wherein the weight ratio of the benzyl ester of the compound of
formula (I) to amidosulfuron is about 1:1.1. With respect to the
methods, in certain embodiments, the methods comprise contacting
the undesirable vegetation or locus thereof or applying to the soil
or water to prevent the emergence or growth of vegetation a
composition described herein. In certain embodiments, the
composition is applied at an application rate of from about 10
grams active ingredient per hectare (gai/ha) to about 340 gai/ha
based on the total amount of active ingredients in the composition.
In certain embodiments, the composition is applied at an
application rate of from about 12 grams active ingredient per
hectare (gai/ha) to about 110 gai/ha based on the total amount of
active ingredients in the composition. In some embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation with a compound of formula (I) or salt or
ester thereof and amidosulfuron or salt thereof, e.g., sequentially
or simultaneously. In some embodiments, the amidosulfuron or salt
thereof is applied at a rate from about 8 gai/ha to about 40 gai/ha
and the compound of formula (I) of salt or ester thereof is applied
at a rate from about 2 g acid equivalent per hectare (gae/ha) to
about 300 gae/ha. In some embodiments, the amidosulfuron or salt
thereof is applied at a rate from about 4 gai/ha to about 24 gai/ha
and the compound of formula (I) of salt or ester thereof is applied
at a rate from about 3.5 g acid equivalent per hectare (gae/ha) to
about 20 gae/ha. In some embodiments, the amidosulfuron or salt
thereof is applied at a rate from about 8 gai/ha to about 12 gai/ha
and the compound of formula (I) of salt or ester thereof is applied
at a rate from about 7 g acid equivalent per hectare (gae/ha) to
about 10 gae/ha. In some embodiments, the amidosulfuron or salt
thereof is applied at a rate of about 10 gai/ha and the compound of
formula (I) of salt or ester thereof is applied at a rate of about
8.75 g acid equivalent per hectare (gae/ha). In certain
embodiments, the methods utilize the benzyl ester of the compound
of formula (I) and amidosulfuron. In one embodiment, the methods
utilize the benzyl ester of the compound of formula (I) and
amidosulfuron, wherein the benzyl ester of the compound of formula
(I) is applied at a rate of about 8.75 gai/ha, and the
amidosulfuron is applied at a rate of about 10 gai/ha. In certain
embodiments, the methods and compositions utilizing the compound of
formula (I) or salt or ester thereof in combination with
amidosulfuron or salt thereof are used to control GALAP, LAMPU, or
VERPE.
[0203] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with azimsulfuron or salt thereof.
With respect to the composition, in some embodiments, the weight
ratio of the compound of formula (I) or salt or ester thereof to
azimsulfuron or salt thereof is within the range of from about 1:15
to about 120:1. In certain embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to azimsulfuron or
salt thereof is within the range of from about 1:8 to about 28:1.
In certain embodiments, the weight ratio of the compound of formula
(I) or salt or ester thereof to azimsulfuron or salt thereof is
within the range of from about 28:1 to about 1:3. In certain
embodiments, the weight ratio of the compound of formula (I) or
salt or ester thereof to azimsulfuron or salt thereof is within the
range of from about 14:1 to about 1:1.1. In certain embodiments,
the compositions provided herein comprise the compound of formula
(I) or its benzyl or n-butyl ester and azimsulfuron. In one
embodiment, the composition comprises the compound of formula (I)
and azimsulfuron, wherein the weight ratio of the compound of
formula (I) and azimsulfuron is about 14:1 to about 1.4:1. In one
embodiment, the composition comprises the benzyl ester of the
compound of formula (I) and azimsulfuron, wherein the weight ratio
of the benzyl ester of the compound of formula (I) and azimsulfuron
is about 7:1 to about 1:1.8. In one embodiment, the composition
comprises the n-butyl ester of the compound of formula (I) and
azimsulfuron, wherein the weight ratio of the n-butyl ester of the
compound of formula (I) and azimsulfuron is about 2.8:1 to about
1.4:1. With respect to the methods, in certain embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation a composition described herein. In some
embodiments, the composition is applied at an application rate of
from about 4 grams active ingredient per hectare (gai/ha) to about
330 gai/ha based on the total amount of active ingredients in the
composition. In certain embodiments, the composition is applied at
an application rate of from about 7 grams active ingredient per
hectare (gai/ha) to about 100 gai/ha based on the total amount of
active ingredients in the composition. In some embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation with a compound of formula (I) or salt or
ester thereof and azimsulfuron or salt thereof, e.g., sequentially
or simultaneously. In some embodiments, the azimsulfuron or salt
thereof is applied at a rate from about 2.5 gai/ha to about 30
gai/ha and the compound of formula (I) of salt or ester thereof is
applied at a rate from about 2 gae/ha to about 300 gae/ha. In some
embodiments, the azimsulfuron or salt thereof is applied at a rate
from about 1.3 gai/ha to about 50 gai/ha and the compound of
formula (I) of salt or ester thereof is applied at a rate from
about 2 g acid equivalent per hectare (gae/ha) to about 140 gae/ha.
In some embodiments, the azimsulfuron or salt thereof is applied at
a rate from about 2.5 gai/ha to about 25 gai/ha and the compound of
formula (I) of salt or ester thereof is applied at a rate from
about 4.38 g acid equivalent per hectare (gae/ha) to about 70
gae/ha. In certain embodiments, the methods utilize the compound of
formula (I) or its benzyl or n-butyl ester and azimsulfuron. In one
embodiment, the methods utilize the compound of formula (I) and
azimsulfuron, wherein the compound of formula (I) is applied at a
rate of from about 8.75 g acid equivalent per hectare (gae/ha) to
about 70 gae/ha, and the azimsulfuron is applied at a rate of from
about 2.5 gai/ha to about 25 gai/ha. In one embodiment, the methods
utilize the benzyl ester of the compound of formula (I) and
azimsulfuron, wherein the benzyl ester of the compound of formula
(I) is applied at a rate of from about 4.38 g acid equivalent per
hectare (gae/ha) to about 70 gae/ha, and the azimsulfuron is
applied at a rate of from about 2.5 gai/ha to about 25 gai/ha. In
one embodiment, the methods utilize the n-butyl ester of the
compound of formula (I) and azimsulfuron, wherein the n-butyl ester
of the compound of formula (I) is applied at a rate of from about
17.5 g acid equivalent per hectare (gae/ha) to about 70 gae/ha, and
the azimsulfuron is applied at a rate of about 25 gai/ha. In
certain embodiments, the methods and compositions utilizing the
compound of formula (I) or salt or ester thereof in combination
with amidosulfuron or salt thereof are used to control BRAPP,
LEFCH, ECHCG, ECHOR, or SCPMA.
[0204] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with bensulfuron-methyl or salt,
carboxylic acid, carboxylate salt, or ester thereof. With respect
to the compositions, in some embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to bensulfuron- or
salt, carboxylic acid, carboxylate salt, or ester thereof is within
the range of from about 1:35 to about 17:1. In certain embodiments,
the weight ratio of the compound of formula (I) or salt or ester
thereof to bensulfuron-methyl or salt, carboxylic acid, carboxylate
salt, or ester thereof is within the range of from about 1:16 to
about 10:1. In certain embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to
bensulfuron-methyl or salt, carboxylic acid, carboxylate salt, or
ester thereof is within the range of from 1:0.2 to about 1:16. In
certain embodiments, the weight ratio of the compound of formula
(I) or salt or ester thereof to bensulfuron-methyl or salt,
carboxylic acid, carboxylate salt, or ester thereof is within the
range of from about 1:0.50 to about 1:8. In certain embodiments,
the compositions provided herein comprise the compound of formula
(I), its benzyl or n-butyl ester and bensulfuron-methyl. In one
embodiment, the composition comprises the compound of formula (I)
and bensulfuron-methyl, wherein the weight ratio of the compound of
formula (I) to bensulfuron-methyl is from about 1:2 to about 1:8.
In one embodiment, the composition comprises the benzyl ester of
the compound of formula (I) and bensulfuron-methyl, wherein the
weight ratio of the benzyl ester of the compound of formula (I) to
bensulfuron-methyl is from about 1:0.5 to about 1:8. In one
embodiment, the composition comprises the n-butyl ester of the
compound of formula (I) and bensulfuron-methyl, wherein the weight
ratio of the n-butyl ester of the compound of formula (I) to
bensulfuron-methyl is about 1:0.5 to about 1:4. With respect to the
methods, in certain embodiments, the methods comprise contacting
the undesirable vegetation or locus thereof or applying to the soil
or water to prevent the emergence or growth of vegetation a
composition described herein. In some embodiments, the composition
is applied at an application rate of from about 6 grams active
ingredient per hectare (gai/ha) to about 370 gai/ha based on the
total amount of active ingredients in the composition. In certain
embodiments, the composition is applied at an application rate of
from about 9 grams active ingredient per hectare (gai/ha) to about
120 gai/ha based on the total amount of active ingredients in the
composition. In some embodiments, the methods comprise contacting
the undesirable vegetation or locus thereof or applying to the soil
or water to prevent the emergence or growth of vegetation with a
compound of formula (I) or salt or ester thereof and
bensulfuron-methyl or salt, carboxylic acid, carboxylate salt, or
ester thereof, e.g., sequentially or simultaneously. In some
embodiments, the bensulfuron-methyl or salt, carboxylic acid,
carboxylate salt, or ester thereof is applied at a rate from about
4 gai/ha to about 70 gai/ha and the compound of formula (I) of salt
or ester thereof is applied at a rate from about 2 gae/ha to about
300 gae/ha. In some embodiments, the bensulfuron-methyl or salt,
carboxylic acid, carboxylate salt, or ester thereof is applied at a
rate from about 4 gai/ha to about 140 gai/ha and the compound of
formula (I) of salt or ester thereof is applied at a rate from
about 2 g acid equivalent per hectare (gae/ha) to about 125 gae/ha.
In some embodiments, the bensulfuron-methyl or salt, carboxylic
acid, carboxylate salt, or ester thereof is applied at a rate from
about 4 gai/ha to about 70 gai/ha and the compound of formula (I)
of salt or ester thereof is applied at a rate from about 4 g acid
equivalent per hectare (gae/ha) to about 70 gae/ha. In certain
embodiments, the methods utilize the compound of formula (I) or its
benzyl or n-butyl ester and bensulfuron methyl. In one embodiment,
the methods utilize the compound of formula (I) and
bensulfuron-methyl, wherein the compound of formula (I) is applied
at a rate of from about 4.38 to about 42 gai/ha, and the
bensulfuron-methyl is applied at a rate of from about 4.38 to about
70 gai/ha. In one embodiment, the methods utilize the benzyl ester
of the compound of formula (I) and bensulfuron-methyl, wherein the
benzyl ester of the compound of formula (I) is applied at a rate of
from about 4.38 to about 17.5 gai/ha, and the bensulfuron-methyl is
applied at a rate of from about 4.38 to about 35 gai/ha. In one
embodiment, the methods utilize the n-butyl ester of the compound
of formula (I) and bensulfuron-methyl, wherein the n-butyl ester of
the compound of formula (I) is applied at a rate of from about 4.38
to about 8.75 gai/ha, and the bensulfuron-methyl is applied at a
rate of from about 4.38 to about 17.5 gai/ha. In certain
embodiments, the methods and compositions utilizing the compound of
formula (I) or salt or ester thereof in combination with
bensulfuron-methyl or salt, carboxylic acid, carboxylate salt, or
ester thereof are used to control BRAPP, ECHCG, LEFCH, ECHOR,
SCPMA, or ISCRU.
[0205] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with chlorsulfuron or salt thereof.
With respect to the compositions, in some embodiments, the weight
ratio of the compound of formula (I) or salt or ester thereof to
chlorsulfuron or salt thereof is within the range of from about
1:27 to about 136:1. In certain embodiments, the weight ratio of
the compound of formula (I) or salt or ester thereof to
chlorsulfuron or salt thereof is within the range of from about
1:32 to about 24:1. In certain embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to chlorsulfuron
or salt thereof is within the range of from about 1.5:1 to about
10:1. In certain embodiments, the weight ratio of the compound of
formula (I) or salt or ester thereof to chlorsulfuron or salt
thereof is within the range of from about 3:1 to about 5:1. In
certain embodiments, the weight ratio of the compound of formula
(I) or salt or ester thereof to chlorsulfuron or salt thereof is
about 4:1. In certain embodiments, the compositions provided herein
comprise the benzyl ester of the compound of formula (I) and
chlorsulfuron. In one embodiment, the composition comprises the
benzyl ester of the compound of formula (I) and chlorsulfuron,
wherein the weight ratio of the benzyl ester of the compound of
formula (I) to chlorsulfuron is from about 3:1 to about 5:1. In one
embodiment, the composition comprises the benzyl ester of the
compound of formula (I) and chlorsulfuron, wherein the weight ratio
of the benzyl ester of the compound of formula (I) to chlorsulfuron
is about 4:1. With respect to the methods, in certain embodiments,
the methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation a composition described herein. In some
embodiments, the composition is applied at an application rate of
from about 4 grams active ingredient per hectare (gai/ha) to about
353 gai/ha based on the total amount of active ingredients in the
composition. In certain embodiments, the composition is applied at
an application rate of from about 5 grams active ingredient per
hectare (gai/ha) to about 120 gai/ha based on the total amount of
active ingredients in the composition. In some embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation with a compound of formula (I) or salt or
ester thereof and chlorsulfuron or salt thereof, e.g., sequentially
or simultaneously. In some embodiments, the chlorsulfuron or salt
thereof is applied at a rate from about 2 gai/ha to about 53 gai/ha
and the compound of formula (I) of salt or ester thereof is applied
at a rate from about 2 gae/ha to about 300 gae/ha. In some
embodiments, the chlorsulfuron or salt thereof is applied at a rate
from about 1 gai/ha to about 5 gai/ha and the compound of formula
(I) of salt or ester thereof is applied at a rate from about 6 g
acid equivalent per hectare (gae/ha) to about 10 gae/ha. In some
embodiments, the chlorsulfuron or salt thereof is applied at a rate
from about 1.5 gai/ha to about 3.5 gai/ha and the compound of
formula (I) of salt or ester thereof is applied at a rate from
about 7 g acid equivalent per hectare (gae/ha) to about 9.5 gae/ha.
In some embodiments, the chlorsulfuron or salt thereof is applied
at a rate of about 2.2 gai/ha and the compound of formula (I) of
salt or ester thereof is applied at a rate of about 8.75 g acid
equivalent per hectare (gae/ha). In certain embodiments, the
methods utilize the benzyl ester of the compound of formula (I) and
chlorsulfuron. In one embodiment, the methods utilize the benzyl
ester of the compound of formula (I) and chlorsulfuron, wherein the
benzyl ester of the compound of formula (I) is applied at a rate of
about 8.75 gai/ha, and the amidosulfuron is applied at a rate of
about 2.2 gai/ha. In certain embodiments, the methods and
compositions utilizing the compound of formula (I) or salt or ester
thereof in combination with chlorsulfuron or salt thereof are used
to control VIOTR or CIRAR.
[0206] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with cyclosulfamuron or salt
thereof. With regard to the compositions, in some embodiments, the
weight ratio of the compound of formula (I) or salt or ester
thereof to cyclosulfamuron or salt thereof is within the range of
from about 1:30 to about 68:1. In certain embodiments, the weight
ratio of the compound of formula (I) or salt or ester thereof to
cyclosulfamuron or salt thereof is within the range of from about
1:20 to about 8:1. In certain embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to cyclosulfamuron
or salt thereof is within the range of from about 1:1.5 to about
3:1. In certain embodiments, the compositions comprise the compound
of formula (I) or its benzyl or n-butyl ester and cyclosulfamuron.
With respect to the methods, in certain embodiments, the methods
comprise contacting the undesirable vegetation or locus thereof or
applying to the soil or water to prevent the emergence or growth of
vegetation a composition described herein. In some embodiments, the
composition is applied at an application rate of from about 6 grams
active ingredient per hectare (gai/ha) to about 360 gai/ha based on
the total amount of active ingredients in the composition. In
certain embodiments, the composition is applied at an application
rate of from about 7 grams active ingredient per hectare (gai/ha)
to about 80 gai/ha based on the total amount of active ingredients
in the composition. In some embodiments, the methods comprise
contacting the undesirable vegetation or locus thereof or applying
to the soil or water to prevent the emergence or growth of
vegetation with a compound of formula (I) or salt or ester thereof
and cyclosulfamuron or salt thereof, e.g., sequentially or
simultaneously. In some embodiments, the cyclosulfamuron or salt
thereof is applied at a rate from about 4.4 gai/ha to about 60
gai/ha and the compound of formula (I) of salt or ester thereof is
applied at a rate from about 2 gae/ha to about 300 gae/ha. In
certain embodiments, the methods utilize the compound of formula
(I) or its benzyl or n-butyl ester and cyclosulfamuron. In certain
embodiments, the methods and compositions utilizing the compound of
formula (I) or salt or ester thereof in combination with
cyclosulfamuron or salt thereof are used to control CYPIR and
SCPMA.
[0207] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with ethametsulfuron-methyl or salt,
carboxylic acid, carboxylate salt, or ester thereof. With regard to
the compositions, in some embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to
ethametsulfuron-methyl or salt, carboxylic acid, carboxylate salt,
or ester thereof is within the range of from about 1:15 to about
68:1. In certain embodiments, the weight ratio of the compound of
formula (I) or salt or ester thereof to ethametsulfuron-methyl
salt, carboxylic acid, carboxylate salt, or ester thereof is within
the range of from about 1:9 to about 8:1. In certain embodiments,
the compositions comprise the compound of formula (I) or its benzyl
or n-butyl ester and ethametsulfuron-methyl. With respect to the
methods, in certain embodiments, the methods comprise contacting
the undesirable vegetation or locus thereof or applying to the soil
or water to prevent the emergence or growth of vegetation a
composition described herein. In some embodiments, the composition
is applied at an application rate of from about 6 grams active
ingredient per hectare (gai/ha) to about 330 gai/ha based on the
total amount of active ingredients in the composition. In certain
embodiments, the composition is applied at an application rate of
from about 7 grams active ingredient per hectare (gai/ha) to about
55 gai/ha based on the total amount of active ingredients in the
composition. In some embodiments, the methods comprise contacting
the undesirable vegetation or locus thereof or applying to the soil
or water to prevent the emergence or growth of vegetation with a
compound of formula (I) or salt or ester thereof and
ethametsulfuron-methyl or salt, carboxylic acid, carboxylate salt,
or ester thereof, e.g., sequentially or simultaneously. In some
embodiments, the ethametsulfuron-methyl or salt, carboxylic acid,
carboxylate salt, or ester thereof is applied at a rate from about
4.4 gai/ha to about 30 gai/ha and the compound of formula (I) of
salt or ester thereof is applied at a rate from about 2 gae/ha to
about 300 gae/ha. In certain embodiments, the methods utilize the
compound of formula (I) or its benzyl or n-butyl ester and
ethametsulfuron-methyl.
[0208] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with ethoxysulfuron or salt thereof.
With respect to the compositions, in some embodiments, the weight
ratio of the compound of formula (I) or salt or ester thereof to
ethoxysulfuron or salt or ester thereof is within the range of from
about 1:66 to about 40:1. In certain embodiments, the weight ratio
of the compound of formula (I) or salt or ester thereof to
ethoxysulfuron or salt or ester thereof is within the range of from
about 1:9 to about 6:1. In certain embodiments, the weight ratio of
the compound of formula (I) or salt or ester thereof to
ethoxysulfuron or salt or ester thereof is within the range of from
about 1:4 to about 6:1. In certain embodiments, the weight ratio of
the compound of formula (I) or salt or ester thereof to
ethoxysulfuron or salt thereof is within the range of from 12:1 to
about 0.10:1. In certain embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to ethoxysulfuron
or salt thereof is within the range of from 5.7:1 to about 0.30:1.
In certain embodiments, the compositions provided herein comprise
the compound of formula (I) or its benzyl ester and ethoxysulfuron.
In one embodiment, the composition comprises the compound of
formula (I) and ethoxysulfuron, wherein the weight ratio of the
compound of formula (I) to ethoxysulfuron is from about 5.7:1 to
about 0.71:1. In one embodiment, the composition comprises the
benzyl ester of the compound of formula (I) and ethoxysulfuron,
wherein the weight ratio of the benzyl ester of the compound of
formula (I) to ethoxysulfuron is from about 2.3:1 to about 0.30:1.
With respect to the methods, in certain embodiments, the methods
comprise contacting the undesirable vegetation or locus thereof or
applying to the soil or water to prevent the emergence or growth of
vegetation a composition described herein. In some embodiments, the
composition is applied at an application rate of from about 9 grams
active ingredient per hectare (gai/ha) to about 420 gai/ha based on
the total amount of active ingredients in the composition. In
certain embodiments, the composition is applied at an application
rate of from about 12 grams active ingredient per hectare (gai/ha)
to about 70 gai/ha based on the total amount of active ingredients
in the composition. In some embodiments, the methods comprise
contacting the undesirable vegetation or locus thereof or applying
to the soil or water to prevent the emergence or growth of
vegetation with a compound of formula (I) or salt or ester thereof
and ethoxysulfuron or salt thereof, e.g., sequentially or
simultaneously. In some embodiments, the ethoxysulfuron or salt
thereof is applied at a rate from about 7.5 gai/ha to about 120
gai/ha and the compound of formula (I) of salt or ester thereof is
applied at a rate from about 2 gae/ha to about 300 gae/ha. In some
embodiments, the ethoxysulfuron or salt thereof is applied at a
rate from about 3 gai/ha to about 30 gai/ha and the compound of
formula (I) of salt or ester thereof is applied at a rate from
about 2 g acid equivalent per hectare (gae/ha) to about 80 gae/ha.
In some embodiments, the ethoxysulfuron or salt thereof is applied
at a rate from about 7.5 gai/ha to about 15 gai/ha and the compound
of formula (I) of salt or ester thereof is applied at a rate from
about 4 g acid equivalent per hectare (gae/ha) to about 42 gae/ha.
In certain embodiments, the methods utilize the compound of formula
(I) or its benzyl ester and ethoxysulfuron. In one embodiment, the
methods utilize the compound of formula (I) and ethoxysulfuron,
wherein the compound of formula (I) is applied at a rate of from
about 10.6 to about 42.4 gai/ha, and the ethoxysulfuron is applied
at a rate of from about 7.5 to about 15 gai/ha. In one embodiment,
the methods utilize the compound of formula (I) and ethoxysulfuron,
wherein the compound of formula (I) is applied at a rate of from
about 10.6 to about 120 gai/ha, and the ethoxysulfuron is applied
at a rate of from about 7.5 to about 30 gai/ha. In one embodiment,
the methods utilize the benzyl ester of the compound of formula (I)
and ethoxysulfuron, wherein the benzyl ester of the compound of
formula (I) is applied at a rate of from about 4.38 to about 42.4
ai/ha, and the ethoxysulfuron is applied at a rate of from about
7.5 to about 70 gai/ha. In certain embodiments, the methods and
compositions utilizing the compound of formula (I) or salt or ester
thereof in combination with ethoxysulfuron or salt thereof are used
to control ECHOR, BRAPP, CYPIR, ISCRU or LEFCH.
[0209] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with flazasulfuron or salt thereof.
With respect to the compositions, in some embodiments, the weight
ratio of the compound of formula (I) or salt or ester thereof to
flazasulfuron or salt or ester thereof is within the range of from
about 1:50 to about 68:1. In certain embodiments, the weight ratio
of the compound of formula (I) or salt or ester thereof to
flazasulfuron or salt or ester thereof is within the range of from
1:23 to about 8:1. In certain embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to flazasulfuron
or salt or ester thereof is within the range of from 1:13 to about
1:1. In certain embodiments, the compositions provided herein
comprise the compound of formula (I) or its benzyl or n-butyl ester
and flazasulfuron. With respect to the methods, in certain
embodiments, the methods comprise contacting the undesirable
vegetation or locus thereof or applying to the soil or water to
prevent the emergence or growth of vegetation a composition
described herein. In some embodiments, the composition is applied
at an application rate of from about 6 grams active ingredient per
hectare (gai/ha) to about 400 gai/ha based on the total amount of
active ingredients in the composition. In certain embodiments, the
composition is applied at an application rate of from about 7 grams
active ingredient per hectare (gai/ha) to about 85 gai/ha based on
the total amount of active ingredients in the composition. In some
embodiments, the methods comprise contacting the undesirable
vegetation or locus thereof or applying to the soil or water to
prevent the emergence or growth of vegetation with a compound of
formula (I) or salt or ester thereof and flazasulfuron or salt
thereof, e.g., sequentially or simultaneously. In some embodiments,
the flazasulfuron or salt or ester thereof is applied at a rate
from about 4.4 gai/ha to about 100 gai/ha and the compound of
formula (I) of salt or ester thereof is applied at a rate from
about 2 gae/ha to about 300 gae/ha. In certain embodiments, the
methods utilize the compound of formula (I) or its benzyl of
n-butyl ester and flazasulfuron. In some embodiments, the
flazasulfuron or salt or ester thereof is applied at a rate from
about 25 gai/ha to about 100 gai/ha and the compound of formula (I)
of salt or ester thereof is applied at a rate from about 4 gae/ha
to about 42 gae/ha. In certain embodiments, the methods utilize the
compound of formula (I) or its benzyl of n-butyl ester and
flazasulfuron. In certain embodiments, the methods and compositions
utilizing the compound of formula (I) or salt or ester thereof in
combination with flazasulfuron or salt thereof are used to control
IPOHE, LEFCH or SETFA.
[0210] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with flucetsulfuron or salt thereof.
With regard to the compositions, in some embodiments, the weight
ratio of the compound of formula (I) or salt or ester thereof to
flucetsulfuron or salt thereof is within the range of from about
1:20 to about 60:1. In certain embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to flucetsulfuron
or salt thereof is within the range of from about 1:5 to about 7:1.
In certain embodiments, the weight ratio of the compound of formula
(I) or salt or ester thereof to flucetsulfuron or salt thereof is
within the range of from about 700:1 to about 4:1. In certain
embodiments, the weight ratio of the compound of formula (I) or
salt thereof to flucetsulfuron or salt thereof is within the range
of from about 350:1 to about 9:1. In certain embodiments, the
compositions provided herein comprise the compound of formula (I)
or its benzyl ester and flucetsulfuron. In one embodiment, the
composition comprises the compound of formula (I) and
flucetsulfuron, wherein the weight ratio of the compound of formula
(I) to flucetsulfuron is about 350:1 to about 9:1. In one
embodiment, the composition comprises the benzyl ester of the
compound of formula (I) and flucetsulfuron, wherein the weight
ratio of the benzyl ester of the compound of formula (I) to
flucetsulfuron is about 175:1 to about 40:1. With respect to the
methods, in certain embodiments, the methods comprise contacting
the undesirable vegetation or locus thereof or applying to the soil
or water to prevent the emergence or growth of vegetation a
composition described herein. In some embodiments, the composition
is applied at an application rate of from about 7 grams active
ingredient per hectare (gai/ha) to about 340 gai/ha based on the
total amount of active ingredients in the composition. In certain
embodiments, the composition is applied at an application rate of
from about 10 grams active ingredient per hectare (gai/ha) to about
60 gai/ha based on the total amount of active ingredients in the
composition. In some embodiments, the methods comprise contacting
the undesirable vegetation or locus thereof or applying to the soil
or water to prevent the emergence or growth of vegetation with a
compound of formula (I) or salt or ester thereof and flucetsulfuron
or salt thereof, e.g., sequentially or simultaneously. In some
embodiments, the flucetsulfuron or salt or ester thereof is applied
at a rate from about 5 gai/ha to about 40 gai/ha and the compound
of formula (I) of salt or ester thereof is applied at a rate from
about 2 gae/ha to about 300 gae/ha. In some embodiments, the
flucetsulfuron or salt thereof is applied at a rate from about
0.025 gai/ha to about 0.4 gai/ha and the compound of formula (I) of
salt or ester thereof is applied at a rate from about 2 g acid
equivalent per hectare (gae/ha) to about 70 gae/ha. In some
embodiments, the flucetsulfuron or salt thereof is applied at a
rate from about 0.05 gai/ha to about 0.2 gai/ha and the compound of
formula (I) of salt or ester thereof is applied at a rate from
about 4.38 g acid equivalent per hectare (gae/ha) to about 35
gae/ha. In certain embodiments, the methods utilize the compound of
formula (I) or its benzyl ester and flucetsulfuron. In one
embodiment, the methods utilize the compound of formula (I) and
flucetsulfuron, wherein the compound of formula (I) is applied at a
rate of from about 4.38 to about 35 gai/ha, and the flucetsulfuron
is applied at a rate of from about 0.05 to about 10 gai/ha. In one
embodiment, the methods utilize the benzyl ester of the compound of
formula (I) and flucetsulfuron, wherein the benzyl ester of the
compound of formula (I) is applied at a rate of from about 8.75 to
about 120 gai/ha, and the flucetsulfuron is applied at a rate of
about 0.05 to about 35 gai/ha. In one embodiment, the methods
utilize the benzyl ester of the compound of formula (I) and
flucetsulfuron, wherein the benzyl ester of the compound of formula
(I) is applied at a rate of from about 8.75 to about 17.5 gai/ha,
and the flucetsulfuron is applied at a rate of about 0.1 to about
10 gai/ha.
[0211] In certain embodiments, the methods and compositions
utilizing the compound of formula (I) or salt or ester thereof in
combination with flucetsulfuron or salt thereof are used to control
LEFCH, IPOHE, CYPIR, BRAPP, SCPJU, or ECHOR.
[0212] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with flupyrsulfuron-methyl sodium or
non-ionic form, carboxylic acid, carboxylate salt, or ester thereof
or other flupyrsulfuron-methyl salt. With respect to the
compositions, in some embodiments, the weight ratio of the compound
of formula (I) or salt or ester thereof to flupyrsulfuron-methyl
sodium or non-ionic form, carboxylic acid, carboxylate salt, or
ester thereof or other flupyrsulfuron-methyl salt is within the
range of from about 1:10 to about 150:1. In certain embodiments,
the weight ratio of the compound of formula (I) or salt or ester
thereof to flupyrsulfuron-methyl sodium or non-ionic form,
carboxylic acid, carboxylate salt, or ester thereof or other
flupyrsulfuron-methyl salt is within the range of from about 1:2 to
about 35:1. In certain embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to
flupyrsulfuron-methyl sodium or non-ionic form, carboxylic acid,
carboxylate salt, or ester thereof or other flupyrsulfuron-methyl
salt is within the range of from about 3.5:1 to about 0.90:1. In
certain embodiments, the weight ratio of the compound of formula
(I) or salt or ester thereof to flupyrsulfuron-methyl sodium or
non-ionic form, carboxylic acid, carboxylate salt, or ester thereof
or other flupyrsulfuron-methyl salt is about 1.75:1. In certain
embodiments, the compositions provided herein comprise the benzyl
ester of the compound of formula (I) and flupyrsulfuron-methyl
sodium. In one embodiment, the composition comprises the benzyl
ester of the compound of formula (I) and flupyrsulfuron-methyl
sodium, wherein the weight ratio of the benzyl ester of the
compound of formula (I) to flupyrsulfuron-methyl sodium is about
1.75:1. With respect to the methods, in certain embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation a composition described herein. In some
embodiments, the composition is applied at an application rate of
from about 4 grams active ingredient per hectare (gai/ha) to about
320 gai/ha based on the total amount of active ingredients in the
composition. In certain embodiments, the composition is applied at
an application rate of from about 10 grams active ingredient per
hectare (gai/ha) to about 90 gai/ha based on the total amount of
active ingredients in the composition. In some embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation with a compound of formula (I) or salt or
ester thereof and flupyrsulfuron-methyl sodium or non-ionic form,
carboxylic acid, carboxylate salt, or ester thereof or other
flupyrsulfuron-methyl salt, e.g., sequentially or simultaneously.
In some embodiments, the flupyrsulfuron-methyl sodium or non-ionic
form, carboxylic acid, carboxylate salt, or ester thereof or other
flupyrsulfuron-methyl salt is applied at a rate from about 2 gai/ha
to about 20 gai/ha and the compound of formula (I) of salt or ester
thereof is applied at a rate from about 2 gae/ha to about 300
gae/ha. In some embodiments, the flupyrsulfuron-methyl sodium or
non-ionic form, carboxylic acid, carboxylate salt, or ester thereof
or other flupyrsulfuron-methyl salt is applied at a rate from about
2.5 gai/ha to about 10 gai/ha and the compound of formula (I) of
salt or ester thereof is applied at a rate from about 4 g acid
equivalent per hectare (gae/ha) to about 17 gae/ha. In some
embodiments, the flupyrsulfuron-methyl sodium or non-ionic form,
carboxylic acid, carboxylate salt, or ester thereof or other
flupyrsulfuron-methyl salt thereof is applied at a rate from about
4 to about 6 gai/ha and the compound of formula (I) of salt or
ester thereof is applied at a rate about 7 to about 10 gae/ha. In
certain embodiments, the methods utilize the benzyl ester of the
compound of formula (I) and flupyrsulfuron-methyl sodium. In one
embodiment, the methods utilize the benzyl ester of the compound of
formula (I) and flupyrsulfuron-methyl sodium, wherein the benzyl
ester of the compound of formula (I) is applied at a rate of about
8.75 gai/ha, and the flupyrsulfuron-methyl sodium is applied at a
rate of about 5 gai/ha. In certain embodiments, the methods and
compositions utilizing the compound of formula (I) or salt or ester
thereof in combination with flupyrsulfuron-methyl sodium or salt
thereof are used to control VERPE or CIRAR.
[0213] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with foramsulfuron or salt thereof.
With respect to the compositions, in some embodiments, the weight
ratio of the compound of formula (I) or salt or ester thereof to
foramsulfuron or salt thereof is within the range of from about
1:30 to about 68:1. In certain embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to foramsulfuron
or salt thereof is within the range of from about 1:18 to about
8:1. In certain embodiments, the weight ratio of the compound of
formula (I) or salt or ester thereof to foramsulfuron or salt
thereof is within the range of from about 1:5 to about 2:1. In
certain embodiments, the compositions provided herein comprise the
compound of formula (I) or its benzyl or n-butyl ester and
foramsulfuron. With respect to the methods, in certain embodiments,
the methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation a composition described herein. In some
embodiments, the composition is applied at an application rate of
from about 6 grams active ingredient per hectare (gai/ha) to about
360 gai/ha based on the total amount of active ingredients in the
composition. In certain embodiments, the composition is applied at
an application rate of from about 7 grams active ingredient per
hectare (gai/ha) to about 75 gai/ha based on the total amount of
active ingredients in the composition. In some embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation with a compound of formula (I) or salt or
ester thereof and foramsulfuron or salt thereof, e.g., sequentially
or simultaneously. In some embodiments, the foramsulfuron or salt
thereof is applied at a rate from about 4.4 gai/ha to about 60
gai/ha and the compound of formula (I) of salt or ester thereof is
applied at a rate from about 2 gae/ha to about 300 gae/ha. In some
embodiments, the foramsulfuron or salt thereof is applied at a rate
from about 4.4 gai/ha to about 40 gai/ha and the compound of
formula (I) of salt or ester thereof is applied at a rate from
about 4 gae/ha to about 100 gae/ha. In certain embodiments, the
methods utilize compound of formula (I) or its benzyl or n-butyl
ester and foramsulfuron. In certain embodiments, the methods and
compositions utilizing the compound of formula (I) or salt or ester
thereof in combination with foramsulfuron or salt thereof are used
to control LEFCH.
[0214] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with imazosulfuron or salt thereof.
With respect to the compositions, in some embodiments, the weight
ratio of the compound of formula (I) or salt or ester thereof to
imazosulfuron or salt thereof is within the range of from about
1:500 to about 14:1. In certain embodiments, the weight ratio of
the compound of formula (I) or salt or ester thereof to
imazosulfuron or salt thereof is within the range of from about
1:18 to about 4:1. In certain embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to imazosulfuron
or salt thereof is within the range of from about 1:0.60 to about
1:20. In certain embodiments, the weight ratio of the compound of
formula (I) or salt or ester thereof to imazosulfuron or salt
thereof is within the range of from about 1:1.2 to about 1:10.3. In
certain embodiments, the compositions provided herein comprise the
compound of formula (I) or its benzyl or n-butyl ester and
imazosulfuron. In one embodiment, the composition comprises the
compound of formula (I) and imazosulfuron, wherein the weight ratio
of the compound of formula (I) and imazosulfuron is from about
1:1.2 to about 1:5.1. In one embodiment, the composition comprises
the benzyl ester of the compound of formula (I) and imazosulfuron,
wherein the weight ratio of the benzyl ester of the compound of
formula (I) and imazosulfuron is from about 1:1.2 to about 1:10.3.
In one embodiment, the composition comprises the n-butyl ester of
the compound of formula (I) and imazosulfuron, wherein the weight
ratio of the n-butyl ester of the compound of formula (I) and
imazosulfuron is from about 1:2.4 to about 1:4.8. With respect to
the methods, in certain embodiments, the methods comprise
contacting the undesirable vegetation or locus thereof or applying
to the soil or water to prevent the emergence or growth of
vegetation a composition described herein. In some embodiments, the
composition is applied at an application rate of from about 23
grams active ingredient per hectare (gai/ha) to about 1300 gai/ha
based on the total amount of active ingredients in the composition.
In certain embodiments, the composition is applied at an
application rate of from about 30 grams active ingredient per
hectare (gai/ha) to about 240 gai/ha based on the total amount of
active ingredients in the composition. In some embodiments, the
imazosulfuron or salt thereof is applied at a rate from about 21
gai/ha to about 1000 gai/ha and the compound of formula (I) of salt
or ester thereof is applied at a rate from about 2 gae/ha to about
300 gae/ha. In some embodiments, the imazosulfuron or salt thereof
is applied at a rate from about 10 gai/ha to about 280 gai/ha and
the compound of formula (I) of salt or ester thereof is applied at
a rate from about 2 g acid equivalent per hectare (gae/ha) to about
140 gae/ha. In some embodiments, the imazosulfuron or salt thereof
is applied at a rate from about 20 gai/ha to about 170 gai/ha and
the compound of formula (I) of salt or ester thereof is applied at
a rate from about 4.38 g acid equivalent per hectare (gae/ha) to
about 70 gae/ha. In certain embodiments, the methods utilize the
compound of formula (I) or its benzyl or n-butyl ester and
imazosulfuron. In one embodiment, the methods utilize the compound
of formula (I) and imazosulfuron, wherein the compound of formula
(I) is applied at a rate of from about 8.75 g acid equivalent per
hectare (gae/ha) to about 70 gae/ha, and the imazosulfuron is
applied at a rate of from about 21 gai/ha to about 168 gai/ha. In
one embodiment, the methods utilize the benzyl ester of the
compound of formula (I) and imazosulfuron, wherein the benzyl ester
of the compound of formula (I) is applied at a rate of from about
4.38 g acid equivalent per hectare (gae/ha) to about 70 gae/ha, and
the imazosulfuron is applied at a rate of from about 21 gai/ha to
about 168 gai/ha. In one embodiment, the methods utilize the
n-butyl ester of the compound of formula (I) and imazosulfuron,
wherein the n-butyl ester of the compound of formula (I) is applied
at a rate of from about 35 g acid equivalent per hectare (gae/ha)
to about 70 gae/ha, and the imazosulfuron is applied at a rate of
about 168 gai/ha. In certain embodiments, the methods and
compositions utilizing the compound of formula (I) or salt or ester
thereof in combination with imazosulfuron or salt thereof are used
to control DIGSA, LEFCH, ECHCO, or SCPMA.
[0215] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with iodosulfuron-methyl sodium or
non-ionic form, carboxylic acid, carboxylate salt, or ester thereof
or other iodosulfuron-methyl salt. With respect to the
compositions, in some embodiments, the weight ratio of the compound
of formula (I) or salt or ester thereof to iodosulfuron-methyl
sodium or non-ionic form, carboxylic acid, carboxylate salt, or
ester thereof or other iodosulfuron-methyl salt is within the range
of from about 1:5 to about 300:1. In certain embodiments, the
weight ratio of the compound of formula (I) or salt or ester
thereof to iodosulfuron-methyl sodium or non-ionic form, carboxylic
acid, carboxylate salt, or ester thereof or other
iodosulfuron-methyl salt is within the range of from about 1:1 to
about 50:1. In certain embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to
iodosulfuron-methyl sodium or non-ionic form, carboxylic acid,
carboxylate salt, or ester thereof or other iodosulfuron-methyl
salt is within the range of from about 9:1 to about 1.2:1. In
certain embodiments, the weight ratio of the compound of formula
(I) or salt or ester thereof to iodosulfuron-methyl sodium or
non-ionic form, carboxylic acid, carboxylate salt, or ester thereof
or other iodosulfuron-methyl salt is within the range of from about
4.5:1 to about 2.5:1. In certain embodiments, the weight ratio of
the compound of formula (I) or salt or ester thereof to
iodosulfuron-methyl sodium or non-ionic form, carboxylic acid,
carboxylate salt, or ester thereof or other iodosulfuron-methyl
salt is about 3.5:1. In certain embodiments, the compositions
provided herein comprise the benzyl ester of the compound of
formula (I) and iodosulfuron-methyl sodium. In one embodiment, the
composition comprises the benzyl ester of the compound of formula
(I) and iodosulfuron-methyl sodium, wherein the weight ratio of the
benzyl ester of the compound of formula (I) to iodosulfuron-methyl
sodium is about 3.5:1. With respect to the methods, in certain
embodiments, the methods comprise contacting the undesirable
vegetation or locus thereof or applying to the soil or water to
prevent the emergence or growth of vegetation a composition
described herein. In some embodiments, the composition is applied
at an application rate of from about 3 grams active ingredient per
hectare (gai/ha) to about 310 gai/ha based on the total amount of
active ingredients in the composition. In certain embodiments, the
composition is applied at an application rate of from about 10
grams active ingredient per hectare (gai/ha) to about 60 gai/ha
based on the total amount of active ingredients in the composition.
In some embodiments, the methods comprise contacting the
undesirable vegetation or locus thereof or applying to the soil or
water to prevent the emergence or growth of vegetation with a
compound of formula (I) or salt or ester thereof and
iodosulfuron-methyl sodium or non-ionic form, carboxylic acid,
carboxylate salt, or ester thereof or other iodosulfuron-methyl
salt, e.g., sequentially or simultaneously. In some embodiments,
the iodosulfuron-methyl sodium or non-ionic form, carboxylic acid,
carboxylate salt, or ester thereof or other iodosulfuron-methyl
salt is applied at a rate from about 1 gai/ha to about 10 gai/ha
and the compound of formula (I) of salt or ester thereof is applied
at a rate from about 2 gae/ha to about 300 gae/ha. In some
embodiments, the iodosulfuron-methyl sodium or non-ionic form,
carboxylic acid, carboxylate salt, or ester thereof or other
iodosulfuron-methyl salt is applied at a rate from about 0.50
gai/ha to about 8 gai/ha and the compound of formula (I) of salt or
ester thereof is applied at a rate from about 3.5 g acid equivalent
per hectare (gae/ha) to about 20 gae/ha. In some embodiments, the
iodosulfuron-methyl sodium or non-ionic form, carboxylic acid,
carboxylate salt, or ester thereof or other iodosulfuron-methyl
salt is applied at a rate from about 1 gai/ha to about 4 gai/ha and
the compound of formula (I) of salt or ester thereof is applied at
a rate from about 7 g acid equivalent per hectare (gae/ha) to about
10 gae/ha. In some embodiments, the iodosulfuron-methyl sodium or
non-ionic form, carboxylic acid, carboxylate salt, or ester thereof
or other iodosulfuron-methyl salt is applied at a rate of about 2.5
gai/ha and the compound of formula (I) of salt or ester thereof is
applied at a rate of about 8.75 g acid equivalent per hectare
(gae/ha). In certain embodiments, the methods utilize the benzyl
ester of the compound of formula (I) and iodosulfuron-methyl
sodium. In one embodiment, the methods utilize the benzyl ester of
the compound of formula (I) and iodosulfuron-methyl sodium, wherein
the benzyl ester of the compound of formula (I) is applied at a
rate of about 8.75 gae/ha to about 32 gae/ha, and the
iodosulfuron-methyl sodium is applied at a rate of about 2.5 gai/ha
to about 5 gai/ha. In certain embodiments, the methods and
compositions utilizing the compound of formula (I) or salt or ester
thereof in combination with iodosulfuron-methyl sodium or non-ionic
form, carboxylic acid, carboxylate salt, or ester thereof or other
iodosulfuron-methyl salt are used to control IPOHE, VIOTR, MATCH,
or CIRAR.
[0216] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with iofensulfuron or salt thereof.
With respect to the compositions, in some embodiments, the weight
ratio of the compound of formula (I) or salt or ester thereof to
iofensulfuron or salt or ester thereof is within the range of from
about 1:25 to about 600:1. In certain embodiments, the weight ratio
of the compound of formula (I) or salt or ester thereof to
iofensulfuron or salt or ester thereof is within the range of from
about 1:9 to about 75:1. In certain embodiments, the compositions
provided herein comprise the compound of formula (I) or its benzyl
or n-butyl ester and iofensulfuron. With respect to the methods, in
certain embodiments, the methods comprise contacting the
undesirable vegetation or locus thereof or applying to the soil or
water to prevent the emergence or growth of vegetation a
composition described herein. In some embodiments, the composition
is applied at an application rate of from about 2.5 grams active
ingredient per hectare (gai/ha) to about 350 gai/ha based on the
total amount of active ingredients in the composition. In certain
embodiments, the composition is applied at an application rate of
from about 3 grams active ingredient per hectare (gai/ha) to about
55 gai/ha based on the total amount of active ingredients in the
composition. In some embodiments, the methods comprise contacting
the undesirable vegetation or locus thereof or applying to the soil
or water to prevent the emergence or growth of vegetation with a
compound of formula (I) or salt or ester thereof and iofensulfuron
or salt thereof, e.g., sequentially or simultaneously. In some
embodiments, the iofensulfuron or salt or ester thereof is applied
at a rate from about 0.5 gai/ha to about 50 gai/ha and the compound
of formula (I) of salt or ester thereof is applied at a rate from
about 2 g acid equivalent per hectare (gae/ha) to about 300 gae/ha.
In certain embodiments, the methods utilize the compound of formula
(I) or its benzyl or n-butyl ester and iofensulfuron.
[0217] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with mesosulfuron-methyl or salt,
carboxylic acid, carboxylate salt, or ester thereof. With respect
to the compositions, in some embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to
mesosulfuron-methyl or salt, carboxylic acid, carboxylate salt, or
ester thereof is within the range of from about 1:8 to about 300:1.
In certain embodiments, the weight ratio of the compound of formula
(I) or salt or ester thereof to mesosulfuron-methyl or salt,
carboxylic acid, carboxylate salt, or ester thereof is within the
range of from 1:2 to about 50:1. In certain embodiments, the weight
ratio of the compound of formula (I) or salt or ester thereof to
mesosulfuron-methyl or salt, carboxylic acid, carboxylate salt, or
ester thereof is within the range of from about 1:1 to about 8:1.
In certain embodiments, the weight ratio of the compound of formula
(I) or salt or ester thereof to mesosulfuron-methyl or salt,
carboxylic acid, carboxylate salt, or ester thereof is within the
range of from about 2:1 to about 4:1. In certain embodiments, the
weight ratio of the compound of formula (I) or salt or ester
thereof to mesosulfuron-methyl or salt, carboxylic acid,
carboxylate salt, or ester thereof is about 2.9:1. In certain
embodiments, the compositions provided herein comprise the benzyl
ester of the compound of formula (I) and mesosulfuron-methyl. In
one embodiment, the composition comprises the benzyl ester of the
compound of formula (I) and mesosulfuron-methyl, wherein the weight
ratio of the benzyl ester of the compound of formula (I) to
mesosulfuron-methyl is about 2.9:1. With respect to the methods, in
certain embodiments, the methods comprise contacting the
undesirable vegetation or locus thereof or applying to the soil or
water to prevent the emergence or growth of vegetation a
composition described herein. In some embodiments, the composition
is applied at an application rate of from about 3 grams active
ingredient per hectare (gai/ha) to about 315 gai/ha based on the
total amount of active ingredients in the composition. In certain
embodiments, the composition is applied at an application rate of
from about 10 grams active ingredient per hectare (gai/ha) to about
65 gai/ha based on the total amount of active ingredients in the
composition. In some embodiments, the methods comprise contacting
the undesirable vegetation or locus thereof or applying to the soil
or water to prevent the emergence or growth of vegetation with a
compound of formula (I) or salt or ester thereof and
mesosulfuron-methyl or salt, carboxylic acid, carboxylate salt, or
ester thereof, e.g., sequentially or simultaneously. In some
embodiments, the mesosulfuron-methyl or salt, carboxylic acid,
carboxylate salt, or ester thereof is applied at a rate from about
1 gai/ha to about 15 gai/ha and the compound of formula (I) of salt
or ester thereof is applied at a rate from about 2 gae/ha to about
300 gae/ha. In some embodiments, the mesosulfuron-methyl salt,
carboxylic acid, carboxylate salt, or ester thereof is applied at a
rate from about 1 gai/ha to about 8 gai/ha and the compound of
formula (I) of salt or ester thereof is applied at a rate from
about 3.5 g acid equivalent per hectare (gae/ha) to about 20
gae/ha. In some embodiments, the mesosulfuron-methyl or salt,
carboxylic acid, carboxylate salt, or ester thereof is applied at a
rate from about 2 gai/ha to about 4 gai/ha and the compound of
formula (I) of salt or ester thereof is applied at a rate from
about 7 g acid equivalent per hectare (gae/ha) to about 10 gae/ha.
In some embodiments, the mesosulfuron-methyl salt, carboxylic acid,
carboxylate salt, or ester thereof is applied at a rate of about 3
gai/ha and the compound of formula (I) of salt or ester thereof is
applied at a rate of about 8.75 g acid equivalent per hectare
(gae/ha). In certain embodiments, the methods utilize the benzyl
ester of the compound of formula (I) and mesosulfuron-methyl. In
one embodiment, the methods utilize the benzyl ester of the
compound of formula (I) and amidosulfuron, wherein the benzyl ester
of the compound of formula (I) is applied at a rate of about 8.75
gai/ha, and the mesosulfuron-methyl is applied at a rate of about 3
gai/ha. In certain embodiments, the methods and compositions
utilizing the compound of formula (I) or salt or ester thereof in
combination with mesosulfuron-methyl or salt, carboxylic acid,
carboxylate salt, or ester thereof are used to control VERPE,
MATCH, or CIRAR.
[0218] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with metsulfuron-methyl or salt,
carboxylic acid, carboxylate salt, or ester thereof. With respect
to the compositions, in some embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to
metsulfuron-methyl or salt, carboxylic acid, carboxylate salt, or
ester thereof is within the range of from about 1:6 to about 300:1.
In certain embodiments, the weight ratio of the compound of formula
(I) or salt or ester thereof to metsulfuron-methyl or salt,
carboxylic acid, carboxylate salt, or ester thereof is within the
range of from 1:30 to about 40:1. In certain embodiments, the
weight ratio of the compound of formula (I) or salt or ester
thereof to metsulfuron-methyl or salt, carboxylic acid, carboxylate
salt, or ester thereof is within the range of from about 16:1 to
about 1:7. In certain embodiments, the weight ratio of the compound
of formula (I) or salt or ester thereof to metsulfuron-methyl or
salt, carboxylic acid, carboxylate salt, or ester thereof is within
the range of from about 8:1 to about 1:3.4. In certain embodiments,
the compositions provided herein comprise the compound of formula
(I) or its benzyl ester and metsulfuron-methyl. In one embodiment,
the composition comprises the compound of formula (I) and
metsulfuron-methyl, wherein the weight ratio of the compound of
formula (I) and metsulfuron-methyl is about 5.7:1 to about 1.1.4.
In one embodiment, the composition comprises the benzyl ester of
the compound of formula (I) and metsulfuron-methyl, wherein the
weight ratio of the benzyl ester of the compound of formula (I) and
metsulfuron-methyl is about 8:1 to about 1:3.4. With respect to the
methods, in certain embodiments, the methods comprise contacting
the undesirable vegetation or locus thereof or applying to the soil
or water to prevent the emergence or growth of vegetation a
composition described herein. In some embodiments, the composition
is applied at an application rate of from about 3 grams active
ingredient per hectare (gai/ha) to about 315 gai/ha based on the
total amount of active ingredients in the composition. In certain
embodiments, the composition is applied at an application rate of
from about 3 grams active ingredient per hectare (gai/ha) to about
75 gai/ha based on the total amount of active ingredients in the
composition. In some embodiments, the methods comprise contacting
the undesirable vegetation or locus thereof or applying to the soil
or water to prevent the emergence or growth of vegetation with a
compound of formula (I) or salt or ester thereof and
metsulfuron-methyl or salt, carboxylic acid, carboxylate salt, or
ester thereof or salt thereof, e.g., sequentially or
simultaneously. In some embodiments, the metsulfuron-methyl or
salt, carboxylic acid, carboxylate salt, or ester thereof is
applied at a rate from about 1 gai/ha to about 15 gai/ha and the
compound of formula (I) of salt or ester thereof is applied at a
rate from about 2 gae/ha to about 300 gae/ha. In some embodiments,
the metsulfuron-methyl or salt, carboxylic acid, carboxylate salt,
or ester thereof is applied at a rate from about 0.50 gai/ha to
about 30 gai/ha and the compound of formula (I) of salt or ester
thereof is applied at a rate from about 1 g acid equivalent per
hectare (gae/ha) to about 84 gae/ha. In some embodiments, the
metsulfuron-methyl or salt, carboxylic acid, carboxylate salt, or
ester thereof is applied at a rate from about 1.1 gai/ha to about
15 gai/ha and the compound of formula (I) of salt or ester thereof
is applied at a rate from about 2.2 g acid equivalent per hectare
(gae/ha) to about 42 gae/ha. In certain embodiments, the methods
utilize the compound of formula (I) or its benzyl ester and
metsulfuron-methyl. In one embodiment, the methods utilize the
compound of formula (I) and metsulfuron-methyl, wherein the
compound of formula (I) is applied at a rate of from about 2.2 g
acid equivalent per hectare (gae/ha) to about 42.4 gae/ha, and the
metsulfuron-methyl is applied at a rate of from about 1.1 gai/ha to
about 15 gai/ha. In one embodiment, the methods utilize the benzyl
ester of the compound of formula (I) and metsulfuron-methyl,
wherein the benzyl ester of the compound of formula (I) is applied
at a rate of from about 4.38 g acid equivalent per hectare (gae/ha)
to about 42.4 gae/ha, and the metsulfuron-methyl is applied at a
rate of from about 1.1 gai/ha to about 15 gai/ha. In certain
embodiments, the methods and compositions utilizing the compound of
formula (I) or salt or ester thereof in combination with
metsulfuron-methyl or salt, carboxylic acid, carboxylate salt, or
ester thereof are used to control BRAPP, ECHOR, MATCH, CIRAR,
SIDSP, CASOB, or POROL.
[0219] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with nicosulfuron or salt thereof.
With respect to the composition, in some embodiments, the weight
ratio of the compound of formula (I) or salt or ester thereof to
nicosulfuron or salt thereof is within the range of from about 1:35
to about 34:1. In certain embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to nicosulfuron or
salt thereof is within the range of from about 1:8 to about 5:1. In
certain embodiments, the weight ratio of the compound of formula
(I) or salt or ester thereof to nicosulfuron or salt thereof is
within the range of from about 5:1 to about 1:13. In certain
embodiments, the weight ratio of the compound of formula (I) or
salt or ester thereof to nicosulfuron or salt thereof is within the
range of from about 2.4:1 to about 1:6.6. In certain embodiments,
the compositions provided herein comprise the compound of formula
(I) or its benzyl ester and nicosulfuron. In one embodiment, the
composition comprises the compound of formula (I) and nicosulfuron,
wherein the weight ratio of the compound of formula (I) and
nicosulfuron is about 2.4:1 to about 1:6.6. In one embodiment, the
composition comprises the benzyl ester of the compound of formula
(I) and nicosulfuron, wherein the weight ratio of the benzyl ester
of the compound of formula (I) and nicosulfuron is about 2:1 to
about 1:4. With respect to the methods, in certain embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation a composition described herein. In some
embodiments, the composition is applied at an application rate of
from about 10 grams active ingredient per hectare (gai/ha) to about
370 gai/ha based on the total amount of active ingredients in the
composition. In certain embodiments, the composition is applied at
an application rate of from about 13 grams active ingredient per
hectare (gai/ha) to about 80 gai/ha based on the total amount of
active ingredients in the composition. In some embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation with a compound of formula (I) or salt or
ester thereof and nicosulfuron or salt thereof, e.g., sequentially
or simultaneously. In some embodiments, the nicosulfuron or salt or
ester thereof is applied at a rate from about 4.4 gai/ha to about
70 gai/ha and the compound of formula (I) of salt or ester thereof
is applied at a rate from about 2 gae/ha to about 300 gae/ha. In
some embodiments, the nicosulfuron or salt thereof is applied at a
rate from about 4 gai/ha to about 70 gai/ha and the compound of
formula (I) of salt or ester thereof is applied at a rate from
about 2 g acid equivalent per hectare (gae/ha) to about 82 gae/ha.
In some embodiments, the nicosulfuron or salt thereof is applied at
a rate from about 8.75 gai/ha to about 35 gai/ha and the compound
of formula (I) of salt or ester thereof is applied at a rate from
about 4.38 g acid equivalent per hectare (gae/ha) to about 42.4
gae/ha. In certain embodiments, the methods utilize the compound of
formula (I) or its benzyl ester and nicosulfuron. In one
embodiment, the methods utilize the compound of formula (I) and
nicosulfuron, wherein the compound of formula (I) is applied at a
rate of from about 5.3 g acid equivalent per hectare (gae/ha) to
about 42.4 gae/ha, and the nicosulfuron is applied at a rate of
from about 8.75 gai/ha to about 35 gai/ha. In one embodiment, the
methods utilize the benzyl ester of the compound of formula (I) and
nicosulfuron, wherein the benzyl ester of the compound of formula
(I) is applied at a rate of from about 4.38 g acid equivalent per
hectare (gae/ha) to about 42.4 gae/ha, and the nicosulfuron is
applied at a rate of from about 8.75 gai/ha to about 35 gai/ha. In
certain embodiments, the methods and compositions utilizing the
compound of formula (I) or salt or ester thereof in combination
with nicosulfuron salt thereof are used to control ECHOR, CYPRO,
LEFCH, DIGSA, CYPES, or CYPIR.
[0220] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with orthosulfamuron or salt
thereof. In some embodiments, the weight ratio of the compound of
formula (I) or salt thereof to orthosulfamuron or salt or ester
thereof is within the range of from about 1:50 to about 40:1. In
certain embodiments, the weight ratio of the compound of formula
(I) or salt or ester thereof to orthosulfamuron or salt thereof is
within the range of from 1:14 to about 11:1. In certain
embodiments, the weight ratio of the compound of formula (I) or
salt or ester thereof to orthosulfamuron or salt thereof is within
the range of from about 1:1 to about 1:14. In certain embodiments,
the weight ratio of the compound of formula (I) or salt or ester
thereof to orthosulfamuron or salt thereof is within the range of
from about 2.3:1 to about 1:6.8. In certain embodiments, the
compositions provided herein comprise the compound of formula (I)
or its benzyl ester and orthosulfamuron. In one embodiment, the
composition comprises the compound of formula (I) and
orthosulfamuron, wherein the weight ratio of the compound of
formula (I) and orthosulfamuron is about 2.3:1 to about 1.3.4. In
one embodiment, the composition comprises the benzyl ester of the
compound of formula (I) and orthosulfamuron, wherein the weight
ratio of the benzyl ester of the compound of formula (I) and
orthosulfamuron is about 2.3:1 to about 1:6.8. With respect to the
methods, in certain embodiments, the methods comprise contacting
the undesirable vegetation or locus thereof or applying to the soil
or water to prevent the emergence or growth of vegetation a
composition described herein. In some embodiments, the composition
is applied at an application rate of from about 9 grams active
ingredient per hectare (gai/ha) to about 400 gai/ha based on the
total amount of active ingredients in the composition. In certain
embodiments, the composition is applied at an application rate of
from about 12 grams active ingredient per hectare (gai/ha) to about
145 gai/ha based on the total amount of active ingredients in the
composition. In some embodiments, the methods comprise contacting
the undesirable vegetation or locus thereof or applying to the soil
or water to prevent the emergence or growth of vegetation with a
compound of formula (I) or salt or ester thereof and
orthosulfamuron or salt thereof, e.g., sequentially or
simultaneously. In some embodiments, the orthosulfamuron or salt
thereof is applied at a rate from about 7.5 gai/ha to about 100
gai/ha and the compound of formula (I) of salt or ester thereof is
applied at a rate from about 2 gae/ha to about 300 gae/ha. In some
embodiments, the orthosulfamuron or salt thereof is applied at a
rate from about 3.8 gai/ha to about 120 gai/ha and the compound of
formula (I) of salt or ester thereof is applied at a rate from
about 2 g acid equivalent per hectare (gae/ha) to about 170 gae/ha.
In some embodiments, the orthosulfamuron or salt thereof is applied
at a rate from about 7.5 gai/ha to about 60 gai/ha and the compound
of formula (I) of salt or ester thereof is applied at a rate from
about 4.38 g acid equivalent per hectare (gae/ha) to about 84.8
gae/ha. In certain embodiments, the methods utilize the compound of
formula (I) or its benzyl ester and orthosulfamuron. In one
embodiment, the methods utilize the compound of formula (I) and
orthosulfamuron, wherein the compound of formula (I) is applied at
a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to
about 84.8 gae/ha, and the orthosulfamuron is applied at a rate of
from about 7.5 gai/ha to about 60 gai/ha. In one embodiment, the
methods utilize the benzyl ester of the compound of formula (I) and
orthosulfamuron, wherein the benzyl ester of the compound of
formula (I) is applied at a rate of from about 4.38 g acid
equivalent per hectare (gae/ha) to about 70 gae/ha, and the
orthosulfamuron is applied at a rate of from about 7.5 gai/ha to
about 60 gai/ha. In certain embodiments, the methods and
compositions utilizing the compound of formula (I) or salt or ester
thereof in combination with orthosulfamuron or salt thereof are
used to control ECHOR, LEFCH, CYPES, BRAPP, CYPIR, DIGSA or
SCPMA.
[0221] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with primisulfuron-methyl or salt,
carboxylic acid, carboxylate salt, or ester thereof. With respect
to the compositions, in some embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to
primisulfuron-methyl or salt, carboxylic acid, carboxylate salt, or
ester thereof is within the range of from about 1:20 to about
120:1. In certain embodiments, the weight ratio of the compound of
formula (I) or salt or ester thereof to primisulfuron-methyl salt,
carboxylic acid, carboxylate salt, or ester thereof is within the
range of from about 1:9 to about 28:1. In certain embodiments, the
weight ratio of the compound of formula (I) or salt or ester
thereof to primisulfuron-methyl salt, carboxylic acid, carboxylate
salt, or ester thereof is within the range of from about 1:4 to
about 2:1. In certain embodiments, the compositions provided herein
comprise the compound of formula (I) or its benzyl or n-butyl ester
and primisulfuron-methyl. With respect to the methods, in certain
embodiments, the methods comprise contacting the undesirable
vegetation or locus thereof or applying to the soil or water to
prevent the emergence or growth of vegetation a composition
described herein. In some embodiments, the composition is applied
at an application rate of from about 5 grams active ingredient per
hectare (gai/ha) to about 340 gai/ha based on the total amount of
active ingredients in the composition. In certain embodiments, the
composition is applied at an application rate of from about 70
grams active ingredient per hectare (gai/ha) to about 110 gai/ha
based on the total amount of active ingredients in the composition.
In some embodiments, the methods comprise contacting the
undesirable vegetation or locus thereof or applying to the soil or
water to prevent the emergence or growth of vegetation with a
compound of formula (I) or salt or ester thereof and
primisulfuron-methyl or salt, carboxylic acid, carboxylate salt, or
ester thereof, e.g., sequentially or simultaneously. In some
embodiments, the primisulfuron-methyl or salt or ester thereof is
applied at a rate from about 2.5 gai/ha to about 40 gai/ha and the
compound of formula (I) of salt or ester thereof is applied at a
rate from about 2 gae/ha to about 300 gae/ha. In some embodiments,
the primisulfuron-methyl or salt or ester thereof is applied at a
rate from about 15 gai/ha to about 30 gai/ha and the compound of
formula (I) of salt or ester thereof is applied at a rate from
about 8 gae/ha to about 20 gae/ha. In certain embodiments, the
methods and compositions utilizing the compound of formula (I) or
salt or ester thereof in combination with the primisulfuron-methyl
or salt or ester thereof are used to control LEFCH.
[0222] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with propyrisulfuron or salt
thereof. With respect to the compositions, in some embodiments, the
weight ratio of the compound of formula (I) or salt or ester
thereof to propyrisulfuron or salt thereof is within the range of
from about 1:50 to about 27:1. In certain embodiments, the weight
ratio of the compound of formula (I) or salt thereof to
propyrisulfuron or salt or ester thereof is within the range of
from 1:10 to about 2:1. In certain embodiments, the weight ratio of
the compound of formula (I) or salt or ester thereof to
propyrisulfuron or salt thereof is within the range of from about
1:0.7 to about 1:20. In certain embodiments, the weight ratio of
the compound of formula (I) or salt or ester thereof to
propyrisulfuron or salt thereof is within the range of from about
1:1.3 to about 1:10.3. In certain embodiments, the compositions
provided herein comprise the compound of formula (I) or its benzyl
ester and propyrisulfuron. In one embodiment, the composition
comprises the compound of formula (I) and propyrisulfuron, wherein
the weight ratio of the compound of formula (I) and propyrisulfuron
is about 1:1.3 to about 1:5.1. In one embodiment, the composition
comprises the benzyl ester of the compound of formula (I) and
propyrisulfuron, wherein the weight ratio of the benzyl ester of
the compound of formula (I) and propyrisulfuron is about 1:2.6 to
about 1:10.3. In one embodiment, the composition comprises the
benzyl ester of the compound of formula (I) and propyrisulfuron,
wherein the weight ratio of the benzyl ester of the compound of
formula (I) and propyrisulfuron is about 1:10 to about 3:1. With
respect to the methods, in certain embodiments, the methods
comprise contacting the undesirable vegetation or locus thereof or
applying to the soil or water to prevent the emergence or growth of
vegetation a composition described herein. The application rate
will depend upon the particular type of weed to be controlled, the
degree of control required, and the timing and method of
application. In some embodiments, the composition is applied at an
application rate of from about 12 grams active ingredient per
hectare (gai/ha) to about 400 gai/ha based on the total amount of
active ingredients in the composition. In some embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation with a compound of formula (I) or salt or
ester thereof and propyrisulfuron or salt thereof, e.g.,
sequentially or simultaneously. In certain embodiments, the
composition is applied at an application rate of from about 15
grams active ingredient per hectare (gai/ha) to about 65 gai/ha
based on the total amount of active ingredients in the composition.
In some embodiments, the propyrisulfuron or salt thereof is applied
at a rate from about 11 gai/ha to about 100 gai/ha and the compound
of formula (I) of salt or ester thereof is applied at a rate from
about 2 gae/ha to about 300 gae/ha. In some embodiments, the
propyrisulfuron or salt thereof is applied at a rate from about 5
gai/ha to about 90 gai/ha and the compound of formula (I) of salt
or ester thereof is applied at a rate from about 2 g acid
equivalent per hectare (gae/ha) to about 40 gae/ha. In some
embodiments, the propyrisulfuron or salt thereof is applied at a
rate from about 11.25 gai/ha to about 45 gai/ha and the compound of
formula (I) of salt or ester thereof is applied at a rate from
about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5
gae/ha. In certain embodiments, the methods utilize the compound of
formula (I) or its benzyl ester and propyrisulfuron. In one
embodiment, the methods utilize the compound of formula (I) and
propyrisulfuron, wherein the compound of formula (I) is applied at
a rate of from about 8.75 g acid equivalent per hectare (gae/ha) to
about 17.5 gae/ha, and the propyrisulfuron is applied at a rate of
from about 22.5 gai/ha to about 45 gai/ha. In one embodiment, the
methods utilize the benzyl ester of the compound of formula (I) and
propyrisulfuron, wherein the benzyl ester of the compound of
formula (I) is applied at a rate of about 4.38 g acid equivalent
per hectare (gae/ha) to about 32 gae/ha, and the propyrisulfuron is
applied at a rate of from about 11.25 gai/ha to about 45 gai/ha. In
certain embodiments, the methods and compositions utilizing the
compound of formula (I) or salt or ester thereof in combination
with propyrisulfuron or salt thereof are used to control BRAPP,
FIMMI, SCPMA or LEFCH.
[0223] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with prosulfuron or salt thereof.
With respect to the compositions, in some embodiments, the weight
ratio of the compound of formula (I) or salt or ester thereof to
prosulfuron or salt thereof is within the range of from about 1:20
to about 68:1. In certain embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to prosulfuron or
salt thereof is within the range of from 1:14 to about 8:1. In
certain embodiments, the compositions provided herein comprise the
compound of formula (I) or its benzyl or n-butyl ester and
prosulfuron. With respect to the methods, in certain embodiments,
the methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation a composition described herein. In some
embodiments, the composition is applied at an application rate of
from about 6 grams active ingredient per hectare (gai/ha) to about
340 gai/ha based on the total amount of active ingredients in the
composition. In certain embodiments, the composition is applied at
an application rate of from about 7 grams active ingredient per
hectare (gai/ha) to about 65 gai/ha based on the total amount of
active ingredients in the composition. In some embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation with a compound of formula (I) or salt or
ester thereof and prosulfuron or salt thereof, e.g., sequentially
or simultaneously. In some embodiments, the prosulfuron or salt
thereof is applied at a rate from about 4.4 gai/ha to about 40
gai/ha and the compound of formula (I) of salt or ester thereof is
applied at a rate from about 2 gae/ha to about 300 gae/ha. In
certain embodiments, the methods utilize the compound of formula
(I) or its benzyl or n-butyl ester and prosulfuron.
[0224] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with pyrimisulfan or salt or ester
thereof. With respect to the compositions, in some embodiments, the
weight ratio of the compound of formula (I) or salt or ester
thereof to pyrimisulfan or salt or ester thereof is within the
range of from about 1:100 to about 30:1. In certain embodiments,
the weight ratio of the compound of formula (I) or salt or ester
thereof to pyrimisulfan or salt or ester thereof is within the
range of from 1:45 to about 10:1. In certain embodiments, the
compositions provided herein comprise the compound of formula (I)
or its benzyl or n-butyl ester and pyrimisulfan. With respect to
the methods, in certain embodiments, the methods comprise
contacting the undesirable vegetation or locus thereof or applying
to the soil or water to prevent the emergence or growth of
vegetation a composition described herein. In some embodiments, the
composition is applied at an application rate of from about 12
grams active ingredient per hectare (gai/ha) to about 500 gai/ha
based on the total amount of active ingredients in the composition.
In certain embodiments, the composition is applied at an
application rate of from about 15 grams active ingredient per
hectare (gai/ha) to about 300 gai/ha based on the total amount of
active ingredients in the composition. In some embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation with a compound of formula (I) or salt or
ester thereof and pyrimisulfan or salt or ester thereof, e.g.,
sequentially or simultaneously. In some embodiments, the
pyrimisulfan or salt or ester thereof is applied at a rate from
about 10 gai/ha to about 200 gai/ha and the compound of formula (I)
of salt or ester thereof is applied at a rate from about 2 gae/ha
to about 300 gae/ha. In certain embodiments, the methods utilize
compound of formula (I) or its benzyl or n-butyl ester and
pyrimisulfan.
[0225] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with pyroxasulfone or salt thereof.
With regard to the compositions, in some embodiments, the weight
ratio of the compound of formula (I) or salt or ester thereof to
pyroxasulfone or salt thereof is within the range of from about
1:500 to about 3:1. In certain embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to pyroxasulfone
or salt thereof is within the range of from 1:136 to about 1:2. In
certain embodiments, the compositions provided herein comprise the
compound of formula (I) or its benzyl or n-butyl ester and
pyroxasulfone. With respect to the methods, in certain embodiments,
the methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation a composition described herein. In some
embodiments, the composition is applied at an application rate of
from about 102 grams active ingredient per hectare (gai/ha) to
about 1300 gai/ha based on the total amount of active ingredients
in the composition. In certain embodiments, the composition is
applied at an application rate of from about 105 grams active
ingredient per hectare (gai/ha) to about 350 gai/ha based on the
total amount of active ingredients in the composition. In some
embodiments, the methods comprise contacting the undesirable
vegetation or locus thereof or applying to the soil or water to
prevent the emergence or growth of vegetation with a compound of
formula (I) or salt or ester thereof and pyroxasulfone or salt
thereof, e.g., sequentially or simultaneously. In some embodiments,
the pyroxasulfone or salt thereof is applied at a rate from about
100 gai/ha to about 1000 gai/ha and the compound of formula (I) of
salt or ester thereof is applied at a rate from about 2 g acid
equivalent per hectare (gae/ha) to about 300 gae/ha. In certain
embodiments, the methods utilize the compound of formula (I) or its
benzyl or n-butyl ester and pyroxasulfone.
[0226] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with rimsulfuron or salt thereof.
With respect to the compositions, in some embodiments, the weight
ratio of the compound of formula (I) or salt or ester thereof to
rimsulfuron or salt or thereof is within the range of from about
1:10 to about 100:1. In certain embodiments, the weight ratio of
the compound of formula (I) or salt or ester thereof to rimsulfuron
or salt thereof is within the range of from about 1:4 to about
10:1. In certain embodiments, the weight ratio of the compound of
formula (I) or salt or ester thereof to rimsulfuron or salt thereof
is within the range of from about 19:1 to about 1:4. In certain
embodiments, the weight ratio of the compound of formula (I) or
salt or ester thereof to rimsulfuron or salt thereof is within the
range of from about 9.7:1 to about 1:2. In certain embodiments, the
compositions provided herein comprise the compound of formula (I)
or its benzyl ester and rimsulfuron. In one embodiment, the
composition comprises the compound of formula (I) and rimsulfuron,
wherein the weight ratio of the compound of formula (I) and
rimsulfuron is about 9.7:1 to about 1:1.7. In one embodiment, the
composition comprises the benzyl ester of the compound of formula
(I) and rimsulfuron, wherein the weight ratio of the benzyl ester
of the compound of formula (I) and rimsulfuron is about 8:1 to
about 1:2. With respect to the methods, in certain embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation a composition described herein. In some
embodiments, the composition is applied at an application rate of
from about 5 grams active ingredient per hectare (gai/ha) to about
320 gai/ha based on the total amount of active ingredients in the
composition. In certain embodiments, the composition is applied at
an application rate of from about 7 grams active ingredient per
hectare (gai/ha) to about 51 gai/ha based on the total amount of
active ingredients in the composition. In some embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation with a compound of formula (I) or salt or
ester thereof and rimsulfuron or salt thereof, e.g., sequentially
or simultaneously. In some embodiments, the rimsulfuron or salt or
ester thereof is applied at a rate from about 3 gai/ha to about 20
gai/ha and the compound of formula (I) of salt or ester thereof is
applied at a rate from about 2 gae/ha to about 300 gae/ha. In some
embodiments, the rimsulfuron or salt thereof is applied at a rate
from about 1 gai/ha to about 20 gai/ha and the compound of formula
(I) of salt or ester thereof is applied at a rate from about 2 g
acid equivalent per hectare (gae/ha) to about 85 gae/ha. In some
embodiments, the rimsulfuron or salt thereof is applied at a rate
from about 2.2 gai/ha to about 8.75 gai/ha and the compound of
formula (I) of salt or ester thereof is applied at a rate from
about 4.38 g acid equivalent per hectare (gae/ha) to about 42
gae/ha. In certain embodiments, the methods utilize the compound of
formula (I) or its benzyl ester and rimsulfuron. In one embodiment,
the methods utilize the compound of formula (I) and rimsulfuron,
wherein the compound of formula (I) is applied at a rate of from
about 5.3 g acid equivalent per hectare (gae/ha) to about 43
gae/ha, and the rimsulfuron is applied at a rate of from about 4.4
gai/ha to about 8.8 gai/ha. In one embodiment, the methods utilize
the benzyl ester of the compound of formula (I) and rimsulfuron,
wherein the benzyl ester of the compound of formula (I) is applied
at a rate of from about 4.4 g acid equivalent per hectare (gae/ha)
to about 42 gae/ha, and the rimsulfuron is applied at a rate of
from about 2.2 gai/ha to about 8.8 gai/ha. In certain embodiments,
the methods and compositions utilizing the compound of formula (I)
or salt or ester thereof in combination with rimsulfuron or salt
thereof are used to control IPOHE, CYPES, DIGSA, LEFCH, CYPRO, and
ECHCG.
[0227] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with sulfometuron-methyl or salt,
carboxylic acid, carboxylate salt, or ester thereof. With respect
to the compositions, in some embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to
sulfometuron-methyl or salt, carboxylic acid, carboxylate salt, or
ester thereof is within the range of from about 1:210 to about
30:1. In certain embodiments, the weight ratio of the compound of
formula (I) or salt or ester thereof to sulfometuron-methyl or
salt, carboxylic acid, carboxylate salt, or ester thereof is within
the range of from 1:50 to about 5:1. In certain embodiments, the
compositions provided herein comprise the compound of formula (I)
or its benzyl or n-butyl ester and sulfometuron-methyl. With
respect to the methods, in certain embodiments, the methods
comprise contacting the undesirable vegetation or locus thereof or
applying to the soil or water to prevent the emergence or growth of
vegetation a composition described herein. In some embodiments, the
composition is applied at an application rate of from about 12
grams active ingredient per hectare (gai/ha) to about 720 gai/ha
based on the total amount of active ingredients in the composition.
In certain embodiments, the composition is applied at an
application rate of from about 52 grams active ingredient per
hectare (gai/ha) to about 150 gai/ha based on the total amount of
active ingredients in the composition. In some embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation with a compound of formula (I) or salt or
ester thereof and sulfometuron-methyl or salt, carboxylic acid,
carboxylate salt, or ester thereof, e.g., sequentially or
simultaneously. In some embodiments, the sulfometuron-methyl or
salt, carboxylic acid, carboxylate salt, or ester thereof is
applied at a rate from about 10 gai/ha to about 420 gai/ha and the
compound of formula (I) of salt or ester thereof is applied at a
rate from about 2 gae/ha to about 300 gae/ha. In certain
embodiments, the methods utilize the compound of formula (I) or its
benzyl or n-butyl ester and sulfometuron-methyl. In some
embodiments, the sulfometuron-methyl or salt, carboxylic acid,
carboxylate salt, or ester thereof is applied at a rate from about
20 gai/ha to about 100 gai/ha and the compound of formula (I) of
salt or ester thereof is applied at a rate from about 2 gae/ha to
about 32 gae/ha. In certain embodiments, the methods utilize the
compound of formula (I) or its benzyl or n-butyl ester and
sulfometuron-methyl. In certain embodiments, the methods and
compositions utilizing the compound of formula (I) or salt or ester
thereof in combination with sulfometuron-methyl or salt, carboxylic
acid, carboxylate salt, or ester thereof are used to control
DIGSA.
[0228] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with sulfosulfuron or salt or ester
thereof. In some embodiments, the weight ratio of the compound of
formula (I) or salt or ester thereof to sulfosulfuron or salt or
ester thereof is within the range of from about 1:35 to about 68:1.
In certain embodiments, the weight ratio of the compound of formula
(I) or salt or ester thereof to sulfosulfuron or salt or ester
thereof is within the range of from 1:11 to about 2:1. The
application rate will depend upon the particular type of weed to be
controlled, the degree of control required, and the timing and
method of application. In some embodiments, the composition is
applied at an application rate of from about 6 grams active
ingredient per hectare (gai/ha) to about 370 gai/ha based on the
total amount of active ingredients in the composition. In certain
embodiments, the composition is applied at an application rate of
from about 9 grams active ingredient per hectare (gai/ha) to about
100 gai/ha based on the total amount of active ingredients in the
composition. In some embodiments, the sulfosulfuron or salt or
ester thereof is applied at a rate from about 4 gai/ha to about 70
gai/ha and the compound of formula (I) of salt or ester thereof is
applied at a rate from about 2 gae/ha to about 300 gae/ha. In some
embodiments, the sulfosulfuron or salt or ester thereof is applied
at a rate from about 4 gai/ha to about 20 gai/ha and the compound
of formula (I) of salt or ester thereof is applied at a rate from
about 4 gae/ha to about 32 gae/ha. In certain embodiments, the
methods and compositions utilizing the compound of formula (I) or
salt or ester thereof in combination with sulfosulfuron or salt,
carboxylic acid, carboxylate salt, or ester thereof are used to
control CIRAR, LAMPA, MATCH or VERPE.
[0229] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with thifensulfuron-methyl or salt,
carboxylic acid, carboxylate salt, or ester thereof. With respect
to the compositions, in some embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to
thifensulfuron-methyl or salt, carboxylic acid, carboxylate salt,
or ester thereof is within the range of from about 1:17 to about
136:1. In certain embodiments, the weight ratio of the compound of
formula (I) or salt or ester thereof to thifensulfuron-methyl or
salt, carboxylic acid, carboxylate salt, or ester thereof is within
the range of from 1:7 to about 4:1. In certain embodiments, the
weight ratio of the compound of formula (I) or salt or ester
thereof to thifensulfuron-methyl or salt, carboxylic acid,
carboxylate salt, or ester thereof is within the range of from
about 0.70:1 to about 10:1. In certain embodiments, the weight
ratio of the compound of formula (I) or salt or ester thereof to
thifensulfuron-methyl or salt, carboxylic acid, carboxylate salt,
or ester thereof is within the range of from about 1.5:1 to about
5:1. In certain embodiments, the weight ratio of the compound of
formula (I) or salt or ester thereof to thifensulfuron-methyl or
salt, carboxylic acid, carboxylate salt, or ester thereof is about
2.3.1. In certain embodiments, the compositions provided herein
comprise the benzyl ester of the compound of formula (I) and
thifensulfuron-methyl. In one embodiment, the composition comprises
the benzyl ester of the compound of formula (I) and
thifensulfuron-methyl, wherein the weight ratio of the benzyl ester
of the compound of formula (I) to thifensulfuron-methyl is about
2.3:1. With respect to the methods, in certain embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation a composition described herein. In some
embodiments, the composition is applied at an application rate of
from about 4 grams active ingredient per hectare (gai/ha) to about
335 gai/ha based on the total amount of active ingredients in the
composition. In certain embodiments, the composition is applied at
an application rate of from about 6 grams active ingredient per
hectare (gai/ha) to about 50 gai/ha based on the total amount of
active ingredients in the composition. In some embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation with a compound of formula (I) or salt or
ester thereof and thifensulfuron-methyl or salt, carboxylic acid,
carboxylate salt, or ester thereof, e.g., sequentially or
simultaneously. In some embodiments, the thifensulfuron-methyl or
salt, carboxylic acid, carboxylate salt, or ester thereof is
applied at a rate from about 2.2 gai/ha to about 35 gai/ha and the
compound of formula (I) of salt or ester thereof is applied at a
rate from about 2 gae/ha to about 300 gae/ha. In some embodiments,
the thifensulfuron-methyl or salt, carboxylic acid, carboxylate
salt, or ester thereof is applied at a rate from about 1 gai/ha to
about 9 gai/ha and the compound of formula (I) of salt or ester
thereof is applied at a rate from about 2 g acid equivalent per
hectare (gae/ha) to about 20 gae/ha. In some embodiments, the
thifensulfuron-methyl or salt, carboxylic acid, carboxylate salt,
or ester thereof is applied at a rate from about 3 gai/ha to about
4.5 gai/ha and the compound of formula (I) of salt or ester thereof
is applied at a rate from about 7 g acid equivalent per hectare
(gae/ha) to about 10 gae/ha. In some embodiments, the
thifensulfuron-methyl or salt, carboxylic acid, carboxylate salt,
or ester thereof is applied at a rate of about 3.8 gai/ha and the
compound of formula (I) of salt or ester thereof is applied at a
rate of about 8.75 g acid equivalent per hectare (gae/ha). In
certain embodiments, the methods utilize the benzyl ester of the
compound of formula (I) and thifensulfuron-methyl. In one
embodiment, the methods utilize the benzyl ester of the compound of
formula (I) and thifensulfuron-methyl, wherein the benzyl ester of
the compound of formula (I) is applied at a rate of about 8.75
gai/ha, and the thifensulfuron-methyl is applied at a rate of about
3.75 gai/ha. In certain embodiments, the methods and compositions
utilizing the compound of formula (I) or salt or ester thereof in
combination with thifensulfuron-methyl or salt, carboxylic acid,
carboxylate salt, or ester thereof are used to control CIRAR.
[0230] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with triafamone or salt thereof.
With respect to the compositions, in some embodiments, the weight
ratio of the compound of formula (I) or salt or ester thereof to
triafamone or salt thereof is within the range of from about 1:25
to about 60:1. In certain embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to triafamone or
salt thereof is within the range of from 1:23 to about 30:1. In
certain embodiments, the compositions provided herein comprise the
compound of formula (I) or its benzyl or n-butyl ester and
triafamone. With respect to the methods, in certain embodiments,
the methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation a composition described herein. In some
embodiments, the composition is applied at an application rate of
from about 7 grams active ingredient per hectare (gai/ha) to about
350 gai/ha based on the total amount of active ingredients in the
composition. In certain embodiments, the composition is applied at
an application rate of from about 7 grams active ingredient per
hectare (gai/ha) to about 200 gai/ha based on the total amount of
active ingredients in the composition. In some embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation with a compound of formula (I) or salt or
ester thereof and triafamone or salt thereof, e.g., sequentially or
simultaneously In some embodiments, the triafamone or salt or ester
thereof is applied at a rate from about 5 gai/ha to about 50 gai/ha
and the compound of formula (I) of salt or ester thereof is applied
at a rate from about 2 gae/ha to about 300 gae/ha. In certain
embodiments, the methods utilize the compound of formula (I) or its
n-butyl or benzyl ester and triafamone.
[0231] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with triasulfuron or salt thereof.
With respect to the compositions, in some embodiments, the weight
ratio of the compound of formula (I) or salt or ester thereof to
triasulfuron or salt thereof is within the range of from about 1:15
to about 136:1. In certain embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to triasulfuron or
salt thereof is within the range of from 1:7 to about 16:1. In
certain embodiments, the compositions provided herein comprise the
compound of formula (I) or its benzyl or n-butyl ester and
triasulfuron. With respect to the methods, in certain embodiments,
the methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation a composition described herein. In some
embodiments, the composition is applied at an application rate of
from about 4 grams active ingredient per hectare (gai/ha) to about
330 gai/ha based on the total amount of active ingredients in the
composition. In certain embodiments, the composition is applied at
an application rate of from about 5 grams active ingredient per
hectare (gai/ha) to about 50 gai/ha based on the total amount of
active ingredients in the composition. In some embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation with a compound of formula (I) or salt or
ester thereof and triasulfuron or salt thereof, e.g., sequentially
or simultaneously. In some embodiments, the triasulfuron or salt
thereof is applied at a rate from about 2.2 gai/ha to about 30
gai/ha and the compound of formula (I) of salt or ester thereof is
applied at a rate from about 2 gae/ha to about 300 gae/ha. In
certain embodiments, the methods utilize the compound of formula
(I) or its benzyl or n-butyl ester and triasulfuron.
[0232] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with tribenuron-methyl or salt,
carboxylic acid, carboxylate salt, or ester thereof. With respect
to the compositions, in some embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to
tribenuron-methyl or salt, carboxylic acid, carboxylate salt, or
ester thereof is within the range of from about 1:100 to about
100:1. In certain embodiments, the weight ratio of the compound of
formula (I) or salt or ester thereof to tribenuron-methyl or salt,
carboxylic acid, carboxylate salt, or ester thereof is within the
range of from 1:100 to about 100:1. In certain embodiments, the
weight ratio of the compound of formula (I) or salt or ester
thereof to tribenuron-methyl or salt, carboxylic acid, carboxylate
salt, or ester thereof is within the range of from about 1.5:1 to
about 10:1. In certain embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to
tribenuron-methyl or salt, carboxylic acid, carboxylate salt, or
ester thereof is within the range of from about 3:1 to about 5:1.
In certain embodiments, the weight ratio of the compound of formula
(I) or salt or ester thereof to tribenuron-methyl or salt,
carboxylic acid, carboxylate salt, or ester thereof is about 4:1.
In certain embodiments, the compositions provided herein comprise
the benzyl ester of the compound of formula (I) and
tribenuron-methyl. In one embodiment, the composition comprises the
benzyl ester of the compound of formula (I) and tribenuron-methyl,
wherein the weight ratio of the benzyl ester of the compound of
formula (I) to tribenuron-methyl is about 4:1. With respect to the
methods, in certain embodiments, the methods comprise contacting
the undesirable vegetation or locus thereof or applying to the soil
or water to prevent the emergence or growth of vegetation a
composition described herein. In some embodiments, the composition
is applied at an application rate of from about 1000 grams active
ingredient per hectare (gai/ha) to about 3000 gai/ha based on the
total amount of active ingredients in the composition. In certain
embodiments, the composition is applied at an application rate of
from about 1000 grams active ingredient per hectare (gai/ha) to
about 3000 gai/ha based on the total amount of active ingredients
in the composition. In some embodiments, the methods comprise
contacting the undesirable vegetation or locus thereof or applying
to the soil or water to prevent the emergence or growth of
vegetation with a compound of formula (I) or salt or ester thereof
and tribenuron-methyl or salt, carboxylic acid, carboxylate salt,
or ester thereof, e.g., sequentially or simultaneously. In some
embodiments, the tribenuron-methyl or salt, carboxylic acid,
carboxylate salt, or ester thereof is applied at a rate from about
1000 gai/ha to about 4000 gai/ha and the compound of formula (I) of
salt or ester thereof is applied at a rate from about 2 gae/ha to
about 300 gae/ha. In some embodiments, the tribenuron-methyl or
salt, carboxylic acid, carboxylate salt, or ester thereof is
applied at a rate from about 0.50 gai/ha to about 6 gai/ha and the
compound of formula (I) of salt or ester thereof is applied at a
rate from about 2 g acid equivalent per hectare (gae/ha) to about
20 gae/ha. In some embodiments, the tribenuron-methyl or salt,
carboxylic acid, carboxylate salt, or ester thereof is applied at a
rate from about 1.5 gai/ha to about 3 gai/ha and the compound of
formula (I) of salt or ester thereof is applied at a rate from
about 7 g acid equivalent per hectare (gae/ha) to about 10 gae/ha.
In some embodiments, the tribenuron-methyl or salt, carboxylic
acid, carboxylate salt, or ester thereof is applied at a rate of
about 2.2 gai/ha and the compound of formula (I) of salt or ester
thereof is applied at a rate of about 8.75 g acid equivalent per
hectare (gae/ha). In certain embodiments, the methods utilize the
benzyl ester of the compound of formula (I) and tribenuron-methyl.
In one embodiment, the methods utilize the benzyl ester of the
compound of formula (I) and tribenuron-methyl, wherein the benzyl
ester of the compound of formula (I) is applied at a rate of about
8.75 gai/ha, and the tribenuron-methyl is applied at a rate of
about 2.2 gai/ha. In certain embodiments, the methods and
compositions utilizing the compound of formula (I) or salt or ester
thereof in combination with tribenuron-methyl or salt, carboxylic
acid, carboxylate salt, or ester thereof are used to control MATCH
or CIRAR.
[0233] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with trifloxysulfuron-sodium or
non-ionic form thereof or other trifloxysulfuron salt. With respect
to the compositions, in some embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to
trifloxysulfuron-sodium or non-ionic form thereof or other
trifloxysulfuron salt is within the range of from about 1:25 to
about 600:1. In certain embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to
trifloxysulfuron-sodium or non-ionic form thereof or other
trifloxysulfuron salt is within the range of from 1:15 to about
100:1. In certain embodiments, the weight ratio of the compound of
formula (I) or salt or ester thereof to trifloxysulfuron-sodium or
non-ionic form thereof or other trifloxysulfuron salt is within the
range of from 1:3 to about 1:1. In certain embodiments, the
compositions provided herein comprise the compound of formula (I)
or its benzyl or n-butyl ester and trifloxysulfuron-sodium. With
respect to the methods, in certain embodiments, the methods
comprise contacting the undesirable vegetation or locus thereof or
applying to the soil or water to prevent the emergence or growth of
vegetation a composition described herein. In some embodiments, the
composition is applied at an application rate of from about 2.5
grams active ingredient per hectare (gai/ha) to about 350 gai/ha
based on the total amount of active ingredients in the composition.
In certain embodiments, the composition is applied at an
application rate of from about 7 grams active ingredient per
hectare (gai/ha) to about 80 gai/ha based on the total amount of
active ingredients in the composition. In some embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation with a compound of formula (I) or salt or
ester thereof and trifloxysulfuron-sodium or non-ionic form thereof
or other trifloxysulfuron salt, e.g., sequentially or
simultaneously. In some embodiments, the trifloxysulfuron-sodium or
salt or ester thereof is applied at a rate from about 0.5 gai/ha to
about 50 gai/ha and the compound of formula (I) of salt or ester
thereof is applied at a rate from about 2 gae/ha to about 300
gae/ha. In some embodiments, the trifloxysulfuron-sodium or salt or
ester thereof is applied at a rate from about 10 gai/ha to about 30
gai/ha and the compound of formula (I) of salt or ester thereof is
applied at a rate from about 8 gae/ha to about 32 gae/ha. In
certain embodiments, the methods utilize the compound of formula
(I) or benzyl or n-butyl ester thereof and trifloxysulfuron-sodium.
In certain embodiments, the methods and compositions utilizing the
compound of formula (I) or salt or ester thereof in combination
with trifloxysulfuron-sodium or non-ionic form thereof are used to
control DIGSA.
[0234] The components of the mixtures described herein can be
applied either separately or as part of a multipart herbicidal
system.
[0235] The mixtures described herein can be applied in conjunction
with one or more other herbicides to control a wider variety of
undesirable vegetation. When used in conjunction with other
herbicides, the composition can be formulated with the other
herbicide or herbicides, tank mixed with the other herbicide or
herbicides or applied sequentially with the other herbicide or
herbicides. Some of the herbicides that can be employed in
conjunction with the compositions and methods described herein
include, but are not limited to: 4-CPA; 4-CPB; 4-CPP; 2,4-D; 2,4-D
choline salt, 2,4-D esters and amines, 2,4-DB; 3,4-DA; 3,4-DB;
[0236] 2,4-DEB; 2,4-DEP; 3,4-DP; 2,3,6-TBA; 2,4,5-T; 2,4,5-TB;
acetochlor, acifluorfen, aclonifen, acrolein, alachlor,
allidochlor, alloxydim, allyl alcohol, alorac, ametridione,
ametryn, amibuzin, amicarbazone, aminocyclopyrachlor, aminopyralid,
amiprofos-methyl, amitrole, ammonium sulfamate, anilofos, anisuron,
asulam, atraton, atrazine, azafenidin, aziprotryne, barban, BCPC,
beflubutamid, benazolin, bencarbazone, benfluralin, benfuresate,
bensulide, benthiocarb, bentazon-sodium, benzadox, benzfendizone,
benzipram, benzobicyclon, benzofenap, benzofluor, benzoylprop,
benzthiazuron, bialaphos, bicyclopyrone, bifenox, bilanafos,
bispyribac-sodium, borax, bromacil, bromobonil, bromobutide,
bromofenoxim, bromoxynil, brompyrazon, butachlor, butafenacil,
butamifos, butenachlor, buthidazole, buthiuron, butralin,
butroxydim, buturon, butylate, cacodylic acid, cafenstrole, calcium
chlorate, calcium cyanamide, cambendichlor, carbasulam,
carbetamide, carboxazole chlorprocarb, carfentrazone-ethyl, CDEA,
CEPC, chlomethoxyfen, chloramben, chloranocryl, chlorazifop,
chlorazine, chlorbromuron, chlorbufam, chloreturon, chlorfenac,
chlorfenprop, chlorflurazole, chlorflurenol, chloridazon,
chlorimuron, chlornitrofen, chloropon, chlorotoluron, chloroxuron,
chloroxynil, chlorpropham, chlorthal, chlorthiamid, cinidon-ethyl,
cinmethylin, cinosulfuron, cisanilide, clethodim, cliodinate,
clodinafop-propargyl, clofop, clomazone, clomeprop, cloprop,
cloproxydim, clopyralid, cloransulam-methyl, CMA, copper sulfate,
CPMF, CPPC, credazine, cresol, cumyluron, cyanatryn, cyanazine,
cycloate, cyclopyrimorate, cycloxydim, cycluron, cyhalofop-butyl,
cyperquat, cyprazine, cyprazole, cypromid, daimuron, dalapon,
dazomet, delachlor, desmedipham, desmetryn, di-allate, dicamba,
dichlobenil, dichloralurea, dichlormate, dichlorprop,
dichlorprop-P, diclofop-methyl, diclosulam, diethamquat, diethatyl,
difenopenten, difenoxuron, difenzoquat, diflufenican,
diflufenzopyr, dimefuron, dimepiperate, dimethachlor,
dimethametryn, dimethenamid, dimethenamid-P, dimexano, dimidazon,
dinitramine, dinofenate, dinoprop, dinosam, dinoseb, dinoterb,
diphenamid, dipropetryn, diquat, disul, dithiopyr, diuron, DMPA,
DNOC, DSMA, EBEP, eglinazine, endothal, epronaz, EPTC, erbon,
esprocarb, ethalfluralin, ethbenzamide, ethidimuron, ethiolate,
ethobenzamid, etobenzamid, ethofumesate, ethoxyfen, etinofen,
etnipromid, etobenzanid, EXD, fenasulam, fenoprop, fenoxaprop,
fenoxaprop-P-ethyl, fenoxaprop-P-ethyl+isoxadifen-ethyl,
fenoxasulfone, fenteracol, fenthiaprop, fentrazamide, fenuron,
ferrous sulfate, flamprop, flamprop-M, florasulam, fluazifop,
fluazifop-P-butyl, fluazolate, flucarbazone, fluchloralin,
flufenacet, flufenican, flufenpyr-ethyl, flumetsulam, flumezin,
flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron,
fluorodifen, fluoroglycofen, fluoromidine, fluoronitrofen,
fluothiuron, flupoxam, flupropacil, flupropanate, fluridone,
fluorochloridone, fluoroxypyr, fluoroxypyr-meptyl, flurtamone,
fluthiacet, fomesafen, fosamine, fumiclorac, furyloxyfen,
glufosinate, glufosinate-ammonium, glufosinate-P-ammonium,
glyphosate salts and esters, halauxifen, halauxifen-methyl,
halosafen, haloxydine, haloxyfop-methyl, haloxyfop-P-methyl,
hexachloroacetone, hexaflurate, hexazinone, imazamethabenz,
imazamox, imazapic, imazapyr, imazaquin, imazethapyr, indanofan,
indaziflam, iodobonil, iodomethane, iodosulfuron-methyl
sodium-ethyl-sodium, iofensulfuron, ioxynil, ipazine,
ipfencarbazone, iprymidam, isocarbamid, isocil, isomethiozin,
isonoruron, isopolinate, isopropalin, isoproturon, isouron,
isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, karbutilate,
ketospiradox, lactofen, lenacil, linuron, MAA, MAMA, MCPA esters
and amines, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, medinoterb,
mefenacet, mefluidide, mesoprazine, mesotrione, metam, metamifop,
metamitron, metazachlor, metazosulfuron, metflurazon,
methabenzthiazuron, methalpropalin, methazole, methiobencarb,
methiozolin, methiuron, methometon, methoprotryne, methyl bromide,
methyl isothiocyanate, methyldymron, metobenzuron, metobromuron,
metolachlor, metosulam, metoxuron, metribuzin, molinate, monalide,
monisouron, monochloroacetic acid, monolinuron, monuron,
morfamquat, MSMA, naproanilide, napropamide, naptalam, neburon,
nipyraclofen, nitralin, nitrofen, nitrofluorfen, norflurazon,
noruron, OCH, orbencarb, ortho-dichlorobenzene, oryzalin,
oxadiargyl, oxadiazon, oxapyrazon, oxasulfuron, oxaziclomefone,
oxyfluorfen, paraflufen-ethyl, parafluoron, paraquat, pebulate,
pelargonic acid, pendimethalin, penoxsulam, pentachlorophenol,
pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham,
phenmedipham, phenmedipham-ethyl, phenobenzuron, phenylmercury
acetate, picloram, picolinafen, pinoxaden, piperophos, potassium
arsenite, potassium azide, potassium cyanate, pretilachlor,
procyazine, prodiamine, profluazol, profluralin, profoxydim,
proglinazine, prohexadione-calcium, prometon, prometryn, pronamide,
propachlor, propanil, propaquizafop, propazine, propham,
propisochlor, propoxycarbazone, propyzamide, prosulfalin,
prosulfocarb, proxan, prynachlor, pydanon, pyraclonil,
pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate,
pyrazoxyfen, pyribenzoxim, pyributicarb, pyriclor, pyridafol,
pyridate, pyriftalid, pyriminobac, pyrithiobac-sodium,
pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine,
quinonamid, quizalofop, quizalofop-P-ethyl, rhodethanil,
saflufenacil, S-metolachlor, sebuthylazine, secbumeton, sethoxydim,
siduron, simazine, simeton, simetryn, SMA, sodium arsenite, sodium
azide, sodium chlorate, sulcotrione, sulfallate, sulfentrazone,
sulfosate, sulfuric acid, sulglycapin, swep, SYN-523, TCA, tebutam,
tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil,
terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryn,
tetrafluoron, thenylchlor, thiazafluoron, thiazopyr, thidiazimin,
thidiazuron, thiencarbazone-methyl, thifensulfurn-methyl,
thiobencarb, tiocarbazil, tioclorim, topramezone, tralkoxydim,
tri-allate, triaziflam, tricamba, triclopyr choline salt, triclopyr
esters and salts, tridiphane, trietazine, trifluralin,
triflusulfuron, trifop, trifopsime, trihydroxytriazine, trimeturon,
tripropindan, tritac tritosulfuron, vernolate, xylachlor and salts,
esters, optically active isomers and mixtures thereof.
[0237] The compositions and methods described herein, can further
be used in conjunction with glyphosate,
5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors,
glufosinate, glutamine synthetase inhibitors, dicamba, phenoxy
auxins, pyridyloxy auxins, synthetic auxins, auxin transport
inhibitors, aryloxyphenoxypropionates, cyclohexanediones,
phenylpyrazolines, acetyl CoA carboxylase (ACCase) inhibitors,
imidazolinones, sulfonylureas, pyrimidinylthiobenzoates,
triazolopyrimidines, sulfonylaminocarbonyltriazolinones,
acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS)
inhibitors, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors,
phytoene desaturase inhibitors, carotenoid biosynthesis inhibitors,
protoporphyrinogen oxidase (PPO) inhibitors, cellulose biosynthesis
inhibitors, mitosis inhibitors, microtubule inhibitors, very long
chain fatty acid inhibitors, fatty acid and lipid biosynthesis
inhibitors, photosystem I inhibitors, photosystem II inhibitors,
triazines, and bromoxynil on glyphosate-tolerant, EPSP synthase
inhibitor-tolerant, glufosinate-tolerant, glutamine synthetase
inhibitor-tolerant, dicamba-tolerant, phenoxy auxin-tolerant,
pyridyloxy auxin-tolerant, auxin-tolerant, auxin transport
inhibitor-tolerant, aryloxyphenoxypropionate-tolerant,
cyclohexanedione-tolerant, phenylpyrazoline-tolerant,
ACCase-tolerant, imidazolinone-tolerant, sulfonylurea-tolerant,
pyrimidinylthiobenzoate-tolerant, triazolopyrimidine-tolerant,
sulfonylaminocarbonyltriazolinone-tolerant, ALS- or AHAS-tolerant,
HPPD-tolerant, phytoene desaturase inhibitor-tolerant, carotenoid
biosynthesis inhibitor tolerant, PPO-tolerant, cellulose
biosynthesis inhibitor-tolerant, mitosis inhibitor-tolerant,
microtubule inhibitor-tolerant, very long chain fatty acid
inhibitor-tolerant, fatty acid and lipid biosynthesis
inhibitor-tolerant, photosystem I inhibitor-tolerant, photosystem
II inhibitor-tolerant, triazine-tolerant, bromoxynil-tolerant, and
crops possessing multiple or stacked traits conferring tolerance to
multiple chemistries and/or multiple modes of action via single
and/or multiple resistance mechanisms. In some embodiments, the
compound of formula (I) or salt or ester thereof and complementary
herbicide or salt or ester thereof are used in combination with
herbicides that are selective for the crop being treated and which
complement the spectrum of weeds controlled by these compounds at
the application rate employed. In some embodiments, the
compositions described herein and other complementary herbicides
are applied at the same time, either as a combination formulation,
as a tank mix, or as a sequential application.
[0238] In some embodiments, the compositions described herein are
employed in combination with one or more herbicide safeners, such
as AD-67 (MON 4660), benoxacor, benthiocarb, brassinolide,
cloquintocet (mexyl), cyometrinil, daimuron, dichlormid,
dicyclonon, dimepiperate, disulfoton, fenchlorazole-ethyl,
fenclorim, flurazole, fluxofenim, furilazole, harpin proteins,
isoxadifen-ethyl, jiecaowan, jiecaoxi, mefenpyr-diethyl, mephenate,
naphthalic anhydride (NA), oxabetrinil, R29148 and
N-phenyl-sulfonylbenzoic acid amides, to enhance their selectivity.
In some embodiments, the safeners are employed in rice, cereal,
corn, or maize settings. In some embodiments, the safener is
cloquintocet or an ester or salt thereof. In certain embodiments,
cloquintocet is utilized to antagonize harmful effects of the
compositions on rice and cereals. In some embodiments, the safener
is cloquintocet (mexyl).
[0239] In some embodiments, the compositions described herein are
employed in combination with one or more plant growth regulators,
such as 2,3,5-tri-iodobenzoic acid, IAA, IBA, naphthaleneacetamide,
.alpha.-naphthaleneacetic acids, benzyladenine, 4-hydroxyphenethyl
alcohol, kinetin, zeatin, endothal, ethephon, pentachlorophenol,
thidiazuron, tribufos, aviglycine, maleic hydrazide, gibberellins,
gibberellic acid, abscisic acid, ancymidol, fosamine, glyphosine,
isopyrimol, jasmonic acid, maleic hydrazide, mepiquat,
2,3,5-tri-iodobenzoic acid, morphactins, dichlorflurenol,
flurprimidol, mefluidide, paclobutrazol, tetcyclacis, uniconazole,
brassinolide, brassinolide-ethyl, cycloheximide, ethylene,
methasulfocarb, prohexadione, triapenthenol and trinexapac.
[0240] In some embodiments, the plant growth regulators are
employed in one or more crops or settings, such as rice, cereal
crops, corn, maize, broadleaf crops, oilseed rape/canola, turf,
pineapple, sugarcane, sunflower, pastures, grasslands, rangelands,
fallowland, turf, tree and vine orchards, plantation crops,
vegetables, and non-crop (ornamentals) settings. In some
embodiments, the plant growth regulator is mixed with the compound
of formula (I), or mixed with the compound of formula (I) and a
sulfonylurea to cause a preferentially advantageous effect on
plants.
[0241] In some embodiments, compositions provided herein further
comprise at least one agriculturally acceptable adjuvant or
carrier. Suitable adjuvants or carriers should not be phytotoxic to
valuable crops, particularly at the concentrations employed in
applying the compositions for selective weed control in the
presence of crops, and should not react chemically with herbicidal
components or other composition ingredients. Such mixtures can be
designed for application directly to weeds or their locus or can be
concentrates or formulations that are normally diluted with
additional carriers and adjuvants before application. They can be
solids, such as, for example, dusts, granules, water-dispersible
granules, or wettable powders, or liquids, such as, for example,
emulsifiable concentrates, solutions, emulsions or suspensions.
They can also be provided as a pre-mix or tank mixed.
[0242] Suitable agricultural adjuvants and carriers include, but
are not limited to, crop oil concentrate; nonylphenol ethoxylate;
benzylcocoalkyldimethyl quaternary ammonium salt; blend of
petroleum hydrocarbon, alkyl esters, organic acid, and anionic
surfactant; C.sub.9-C.sub.11 alkylpolyglycoside; phosphated alcohol
ethoxylate; natural primary alcohol (C.sub.12-C.sub.16) ethoxylate;
di-sec-butylphenol EO-PO block copolymer; polysiloxane-methyl cap;
nonylphenol ethoxylate+urea ammonium nitrate; emulsified methylated
seed oil; tridecyl alcohol (synthetic) ethoxylate (8 EO); tallow
amine ethoxylate (15 EO); PEG (400) dioleate-99.
[0243] Liquid carriers that can be employed include water and
organic solvents. The organic solvents include, but are not limited
to, petroleum fractions or hydrocarbons such as mineral oil,
aromatic solvents, paraffinic oils, and the like; vegetable oils
such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower
seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm
oil, peanut oil, safflower oil, sesame oil, tung oil and the like;
esters of the above vegetable oils; esters of monoalcohols or
dihydric, trihydric, or other lower polyalcohols (4-6 hydroxy
containing), such as 2-ethyl hexyl stearate, n-butyl oleate,
isopropyl myristate, propylene glycol dioleate, di-octyl succinate,
di-butyl adipate, di-octyl phthalate and the like; esters of mono,
di and polycarboxylic acids and the like. Specific organic solvents
include, but are not limited to toluene, xylene, petroleum naphtha,
crop oil, acetone, methyl ethyl ketone, cyclohexanone,
trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate,
butyl acetate, propylene glycol monomethyl ether and diethylene
glycol monomethyl ether, methyl alcohol, ethyl alcohol, isopropyl
alcohol, amyl alcohol, ethylene glycol, propylene glycol,
glycerine, N-methyl-2-pyrrolidinone, N,N-dimethyl alkylamides,
dimethyl sulfoxide, liquid fertilizers and the like. In certain
embodiments, Water is the carrier for the dilution of
concentrates.
[0244] Suitable solid carriers include but are not limited to talc,
pyrophyllite clay, silica, attapulgus clay, kaolin clay,
kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate,
bentonite clay, Fuller's earth, cottonseed hulls, wheat flour,
soybean flour, pumice, wood flour, walnut shell flour, lignin,
cellulose, and the like.
[0245] In some embodiments, the compositions described herein
further comprise one or more surface-active agents. In some
embodiments, such surface-active agents are employed in both solid
and liquid compositions, and in certain embodiments those designed
to be diluted with carrier before application. The surface-active
agents can be anionic, cationic or nonionic in character and can be
employed as emulsifying agents, wetting agents, suspending agents,
or for other purposes. Surfactants which may also be used in the
present formulations are described, inter alia, in "McCutcheon's
Detergents and Emulsifiers Annual," MC Publishing Corp., Ridgewood,
N.J., 1998 and in "Encyclopedia of Surfactants," Vol. I-III,
Chemical Publishing Co., New York, 1980-81. Surface-active agents
include, but are not limited to salts of alkyl sulfates, such as
diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as
calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide
addition products, such as nonylphenol-C.sub.18 ethoxylate;
alcohol-alkylene oxide addition products, such as tridecyl
alcohol-C.sub.16 ethoxylate; soaps, such as sodium stearate;
alkyl-naphthalene-sulfonate salts, such as sodium
dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate
salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol
esters, such as sorbitol oleate; quaternary amines, such as lauryl
trimethylammonium chloride; polyethylene glycol esters of fatty
acids, such as polyethylene glycol stearate; block copolymers of
ethylene oxide and propylene oxide; salts of mono and dialkyl
phosphate esters; vegetable or seed oils such as soybean oil,
rapeseed/canola oil, olive oil, castor oil, sunflower seed oil,
coconut oil, corn oil, cottonseed oil, linseed oil, palm oil,
peanut oil, safflower oil, sesame oil, tung oil and the like; and
esters of the above vegetable oils, and in certain embodiments,
methyl esters.
[0246] In some embodiments, these materials, such as vegetable or
seed oils and their esters, can be used interchangeably as an
agricultural adjuvant, as a liquid carrier or as a surface active
agent.
[0247] Other exemplary additives for use in the compositions
provided herein include but are not limited to compatibilizing
agents, antifoam agents, sequestering agents, neutralizing agents
and buffers, corrosion inhibitors, dyes, odorants, spreading
agents, penetration aids, sticking agents, dispersing agents,
thickening agents, freezing point depressants, antimicrobial
agents, and the like. The compositions may also contain other
compatible components, for example, other herbicides, plant growth
regulants, fungicides, insecticides, and the like and can be
formulated with liquid fertilizers or solid, particulate fertilizer
carriers such as ammonium nitrate, urea and the like.
[0248] In some embodiments, the concentration of the active
ingredients in the compositions described herein is from about
0.0005 to 98 percent by weight. In some embodiments, the
concentration is from about 0.0006 to 90 percent by weight. In
compositions designed to be employed as concentrates, the active
ingredients, in certain embodiments, are present in a concentration
from about 0.1 to 98 weight percent, and in certain embodiments
from about 0.5 to 90 weight percent. Such compositions are, in
certain embodiments, diluted with an inert carrier, such as water,
before application. The diluted compositions usually applied to
weeds or the locus of weeds contain, in certain embodiments, about
0.0003 to 65.0 weight percent active ingredient and in certain
embodiments contain about 0.0008 to 32.5 weight percent.
[0249] The present compositions can be applied to weeds or their
locus by the use of conventional ground or aerial dusters,
sprayers, and granule applicators, by addition to irrigation or
paddy water, and by other conventional means known to those skilled
in the art.
[0250] The described embodiments and following examples are for
illustrative purposes and are not intended to limit the scope of
the claims. Other modifications, uses, or combinations with respect
to the compositions described herein will be apparent to a person
of ordinary skill in the art without departing from the spirit and
scope of the claimed subject matter.
EXAMPLES
[0251] Results in Examples I, II, III, IV, and V are greenhouse
trial results.
Example I
Evaluation of Postemergence Foliar-Applied Herbicidal Mixtures for
Weed Control in Direct Seeded Rice
[0252] Seeds or nutlets of the desired test plant species were
planted in a soil matrix prepared by mixing a loam or sandy loam
soil (e.g., 28.6 percent silt, 18.8 percent clay, and 52.6 percent
sand, with a pH of about 5.8 and an organic matter content of about
1.8 percent) and calcareous grit in an 80 to 20 ratio. The soil
matrix was contained in plastic pots with a volume of 1 quart and a
surface area of 83.6 square centimeters (cm.sup.2). When required
to ensure good germination and healthy plants, a fungicide
treatment and/or other chemical or physical treatment was applied.
The plants were grown for 8-22 days in a greenhouse with an
approximate 14 h photoperiod which was maintained at about
29.degree. C. during the day and 26.degree. C. during the night.
Nutrients (Peters Excel.RTM. 15-5-15 5-Ca 2-Mg and iron chelate)
were applied in the irrigation solution as needed and water was
added on a regular basis. Supplemental lighting was provided with
overhead metal halide 1000-Watt lamps as necessary. The plants were
employed for testing when they reached the first through fourth
true leaf stage.
[0253] Treatments consisted of the acid or esters of
4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine--
2-carboxylic acid (Compound A), each formulated as an SC, and
various herbicidal components alone and in combination. Forms of
compound A were applied on an acid equivalent basis.
Forms of compound A (compound of formula I) tested include:
##STR00037##
[0254] Other herbicidal components were applied on an active
ingredient basis and included acetolactate synthase
(ALS)-inhibiting herbicides (sulfonylurea chemical class)
azimsulfuron formulated as Gulliver.RTM., bensulfuron-methyl
formulated as Londax.RTM. 60DF, cyclosulfamuron (technical
material), ethoxysulfuron formulated as Sunrice.RTM. 15 WDG,
flazasulfuron formulated as Katana.RTM., flucetosulfuron formulated
as Sukedachi.RTM. 1KG G, foramsulfuron formulated as Option.RTM.,
imazosulfuron formulated as Brazzos.RTM. WG,
iodosulfuron-methyl-sodium formulated as Hussar.RTM.,
metsulfuron-methyl formulated as Lorate.RTM., nicosulfuron
formulated as Accent.RTM., orthosulfamuron formulated as
Strada.RTM. WG, primisulfuron-methyl (technical material),
propyrisulfuron formulated as Zeta One.RTM., rimsulfuron formulated
as Matrix.RTM. WG, sulfometuron-methyl formulated as Oust.RTM., and
trifloxysulfuron-sodium formulated as Monument.RTM. 75WG.
[0255] Treatment requirements were calculated based upon the rates
being tested, the concentration of active ingredient or acid
equivalent in the formulation, and a 12 mL application volume at a
rate of 187 L/ha.
[0256] For treatments comprised of formulated compounds, measured
amounts of compounds were placed individually in 25 mL glass vials
and diluted in a volume of 1.25% (v/v) Agri-Dex.RTM. crop oil
concentrated to obtain 12.times. stock solutions. If a test
compound did not dissolve readily, the mixture was warmed and/or
sonicated. Application solutions were prepared by adding an
appropriate amount of each stock solution (e.g., 1 mL) and diluted
to the appropriate final concentrations with the addition of 10 mL
of an aqueous mixture of 1.25% (v/v) crop oil concentrate so that
the final spray solutions contained 1.25+/-0.05% (v/v) Agrcrop oil
concentrate.
[0257] For treatments comprised of technical compounds, weighed
amounts can be placed individually in 25 mL glass vials and
dissolved in a volume of 97:3 v/v acetone/DMSO to obtain 12.times.
stock solutions. If a test compound does not dissolve readily, the
mixture can be warmed and/or sonicated. Application solutions can
be prepared by adding an appropriate amount of each stock solution
(e.g., 1 mL) and diluted to the appropriate final concentrations
with the addition of 10 mL of an aqueous mixture of 1.5% (v/v) crop
oil concentrate so that the final spray solutions contain 1.25%
(v/v) crop oil concentrate. When technical materials are used, the
concentrated stock solutions can be added to the spray solutions so
that the final acetone and DMSO concentrations of the application
solutions are 16.2% and 0.5%, respectively.
[0258] For treatments comprised of formulated and technical
compounds, weighed amounts of the technical materials were placed
individually in 25 mL glass vials and dissolved in a volume of 97:3
v/v acetone/DMSO to obtain 12.times. stock solutions, and measured
amounts of the formulated compounds were placed individually in 25
mL glass vials and diluted in a volume of 1.25% (v/v) crop oil
concentrate to obtain 12.times. stock solutions. If a test compound
did not dissolve readily, the mixture was warmed and/or sonicated.
Application solutions were prepared by adding an appropriate amount
of each stock solution (e.g., 1 mL) and diluted to the appropriate
final concentrations with the addition of an appropriate amount of
an aqueous mixture of 1.5% (v/v) crop oil concentrate so that the
final spray solutions contained 1.25% (v/v) crop oil concentrate.
When required, additional water and/or 97:3 v/v acetone/DMSO was
added to individual application solutions so that the final acetone
and DMSO concentrations of the application solutions being compared
were 8.1% and 0.25%, respectively.
[0259] All stock solutions and applications solutions were visually
inspected for compound compatibility prior to application. Spray
solutions were applied to the plant material with an overhead
Mandel track sprayer equipped with an 8002E nozzle calibrated to
deliver 187 L/ha over an application area of 0.503 m.sup.2 at a
spray height of 18 to 20 inches (46 to 50 cm) above average plant
canopy height. Control plants were sprayed in the same manner with
the solvent blank.
[0260] The treated plants and control plants were placed in a
greenhouse as described above and watered by sub-irrigation to
prevent wash-off of the test compounds. After approximately 3
weeks, the condition of the test plants as compared with that of
the untreated plants was determined visually and scored on a scale
of 0 to 100 percent where 0 corresponds to no injury or growth
inhibition and 100 corresponds to complete kill.
[0261] Colby's equation was used to determine the herbicidal
effects expected from the mixtures (Colby, S. R. 1967. Calculation
of the synergistic and antagonistic response of herbicide
combinations. Weeds 15:20-22.).
[0262] The following equation was used to calculate the expected
activity of mixtures containing two active ingredients, A and
B:
Expected=A+B-(A.times.B/100)
[0263] A=observed efficacy of active ingredient A at the same
concentration as used in the mixture.
[0264] B=observed efficacy of active ingredient B at the same
concentration as used in the mixture.
[0265] The compounds tested, application rates employed, plant
species tested, and results are given in Tables 1-27.
TABLE-US-00001 TABLE 1 Synergistic Activity of Foliar-Applied
Compound A Acid and Azimsulfuron Herbicidal Compositions on Weed
Control in a Rice Cropping System. Visual Weed Control (%) -
Compound A 20 DAA Acid Azimsulfuron BRAPP gae/ha gai/ha Obs Exp
4.38 0 10 -- 0 3.125 0 -- 0 6.25 0 -- 0 12.5 60 -- 4.38 3.125 20 10
4.38 6.25 70 10 4.38 12.5 75 64
TABLE-US-00002 TABLE 2 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Azimsulfuron Herbicidal Compositions on
Weed Control in a Rice Cropping System. Visual Weed Control (%) -
Compound A 20 DAA Benzyl Ester Azimsulfuron LEFCH gae/ha gai/ha Obs
Exp 4.38 0 10 -- 8.75 0 20 -- 0 3.125 0 -- 0 6.25 0 -- 4.38 3.125
10 10 8.75 3.125 45 20 4.38 6.25 20 10 8.75 6.25 35 20
TABLE-US-00003 TABLE 3 Synergistic Activity of Foliar-Applied
Compound A Acid and Bensulfuron-methyl Herbicidal Compositions on
Weed Control in a Rice Cropping System. Compound A Bensulfuron-
Acid methyl gae/ha gai/ha Obs Exp Visual Weed Control (%) - 21 DAA
BRAPP 4.38 0 40 -- 0 4.38 0 -- 0 8.75 0 -- 0 17.5 0 -- 4.38 4.38 55
40 4.38 8.75 50 40 4.38 17.5 60 40 4.38 0 50 -- 0 17.5 0 -- 0 35 0
-- 4.38 17.5 65 50 4.38 35 55 50 Visual Weed Control (%) - 21 DAA
ECHCG 4.38 0 15 -- 8.75 0 50 -- 0 17.5 0 -- 0 35 0 -- 4.38 17.5 40
15 8.75 17.5 70 50 4.38 35 40 15 8.75 35 65 50 Visual Weed Control
(%) - 20 DAA LEFCH 19.4 0 5 -- 0 70 5 -- 19.4 70 35 10
TABLE-US-00004 TABLE 4 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Bensulfuron-methyl Herbicidal
Compositions on Weed Control in a Rice Cropping System. Visual Weed
Control (%) - Compound A Bensulfuron- 21 DAA Benzyl Ester methyl
BRAPP gae/ha gai/ha Obs Exp 8.75 0 70 -- 17.5 0 80 -- 0 8.75 0 -- 0
17.5 0 -- 8.75 8.75 80 70 17.5 8.75 95 80 8.75 17.5 85 70 17.5 17.5
90 80 4.38 0 50 -- 8.75 0 80 -- 0 17.5 0 -- 0 35 0 -- 4.38 17.5 75
50 8.75 17.5 95 80 4.38 35 75 50 8.75 35 95 80 Visual Weed Compound
A Bensulfuron- Control (%) - 21 DAA Benzyl Ester methyl ECHCG LEFCH
gae/ha gai/ha Obs Exp Obs Exp 4.38 0 10 -- 0 -- 0 17.5 0 -- 10 -- 0
35 0 -- 10 -- 4.38 17.5 35 10 20 10 4.38 35 30 10 60 10 Visual Weed
Control (%) - Compound A Bensulfuron- 20 DAA Benzyl Ester methyl
ISCRU gae/ha gai/ha Obs Exp 6 0 30 -- 24 0 35 -- 0 70 30 -- 6 70 70
51 24 70 100 55
TABLE-US-00005 TABLE 5 Synergistic Activity of Foliar-Applied
Compound A n-Butyl Ester and Bensulfuron-methyl Herbicidal
Compositions on Weed Control in a Rice Cropping System. Compound A
Bensulfuron- n-Butyl Ester methyl gae/ha gai/ha Obs Exp Visual Weed
Control (%) - 21 DAA BRAPP 4.38 0 0 -- 8.75 0 40 -- 0 4.38 0 -- 0
8.75 0 -- 0 17.5 0 -- 4.38 4.38 40 0 8.75 4.38 55 40 4.38 8.75 20 0
8.75 8.75 50 40 4.38 17.5 50 0 8.75 17.5 30 40 Visual Weed Control
(%) - 27 DAA ECHCG 4.38 0 0 -- 8.75 0 0 -- 0 4.38 0 -- 0 8.75 0 --
0 17.5 0 -- 4.38 4.38 10 0 8.75 4.38 20 0 4.38 8.75 20 0 8.75 8.75
10 0 4.38 17.5 10 0 8.75 17.5 20 0
TABLE-US-00006 TABLE 6 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Cyclosulfamuron Herbicidal Compositions
on Weed Control in a Rice Cropping System. Visual Weed Control (%)
- Compound A 22 DAA Benzyl Ester Cyclosulfamuron CYPIR gae/ha
gai/ha Obs Exp 8 0 10 -- 16 0 60 -- 0 12.5 95 -- 8 12.5 100 96 16
12.5 100 98
TABLE-US-00007 TABLE 7 Synergistic Activity of Foliar-Applied
Compound A Acid and Ethoxysulfuron Herbicidal Compositions on Weed
Control in a Rice Cropping System. Visual Weed Control (%) -
Compound A 22 DAA Acid Ethoxysulfuron CYPIR gae/ha gai/ha Obs Exp 8
0 60 -- 16 0 90 -- 0 7.5 50 -- 0 15 50 -- 8 7.5 95 80 16 7.5 85 95
8 15 99 80 16 15 100 95
TABLE-US-00008 TABLE 8 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Ethoxysulfuron Herbicidal Compositions
on Weed Control in a Rice Cropping System. Compound A Benzyl Ester
Ethoxysulfuron gae/ha gai/ha Obs Exp Visual Weed Control (%) - 22
DAA BRAPP 8 0 50 -- 0 7.5 0 -- 0 15 0 -- 0 30 0 -- 8 7.5 75 50 8 15
65 50 8 30 80 50 Visual Weed Control (%) - 22 DAA CYPIR 8 0 60 --
16 0 80 -- 0 7.5 50 -- 0 15 50 -- 0 30 85 -- 8 7.5 95 80 16 7.5 85
90 8 15 99 80 16 15 100 90 8 30 99 94 16 30 100 97 Visual Weed
Control (%) - 21 DAA ISCRU 8 0 20 -- 16 0 0 -- 0 17.5 0 -- 0 70 0
-- 8 17.5 15 20 16 17.5 25 0 8 70 100 20 16 70 100 0
TABLE-US-00009 TABLE 9 Synergistic Activity of Foliar-Applied
Compound A Acid and Flazasulfuron Herbicidal Compositions on Weed
Control in a Rice Cropping System. Visual Weed Control (%) -
Compound A 22 DAA Acid Flazasulfuron IPOHE gae/ha gai/ha Obs Exp 8
0 25 -- 16 0 35 -- 32 0 40 -- 0 100 50 -- 8 100 75 63 16 100 80 68
32 100 75 70
TABLE-US-00010 TABLE 10 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Flazasulfuron Herbicidal Compositions
on Weed Control in a Rice Cropping System. Visual Weed Control
Compound A 22 % - Benzyl Ester Flazasulfuron 22 DAA gae/ha gai/ha
Obs Exp LEFCH 8 0 0 -- 0 25 0 -- 0 50 10 -- 8 25 20 0 8 50 35 10
IPOHE 8 0 10 -- 16 0 10 -- 32 0 35 -- 0 50 50 -- 0 100 50 -- 8 50
65 55 16 50 65 55 32 50 70 68 8 100 65 55 16 100 85 55 32 100 70
68
TABLE-US-00011 TABLE 11 Synergistic Activity of Foliar-Applied
Compound A Acid and FlucetosulfuronHerbicidal Compositions on Weed
Control in a Rice Cropping System. Compound A Acid Flucetosulfuron
gae/ha gai/ha Obs Exp Visual Weed Control (%) - 21 DAA LEFCH 8.75 0
40 -- 17.5 0 30 -- 0 0.05 0 -- 0 0.1 0 -- 8.75 0.05 55 40 17.5 0.05
40 30 8.75 0.1 35 40 17.5 0.1 60 30 Visual Weed Control (%) - 21
DAA IPOHE 4.38 0 25 -- 8.75 0 30 -- 17.5 0 45 -- 0 0.2 20 -- 4.38
0.2 50 40 8.75 0.2 65 44 17.5 0.2 65 56 Visual Weed Control (%) -
21 DAA CYPIR 4.38 0 70 -- 0 0.05 0 -- 0 0.1 0 -- 0 0.2 20 -- 4.38
0.05 95 70 4.38 0.1 95 70 4.38 0.2 95 76 Visual Weed Control (%) -
22 DAA IPOHE 8 0 25 -- 16 0 35 -- 0 5 90 -- 0 10 90 -- 8 5 95 93 16
5 95 94 8 10 95 93 16 10 99 94
TABLE-US-00012 TABLE 12 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Flucetosulfuron Herbicidal Compositions
on Weed Control in a Rice Cropping System. Visual Weed Control
Compound A (%) - 21 DAA Benzyl Ester Flucetosulfuron IPOHE gae/ha
gai/ha Obs Exp 4.38 0 0 -- 8.75 0 10 -- 17.5 0 30 -- 0 0.05 20 --
4.38 0.05 60 20 8.75 0.05 60 28 17.5 0.05 45 44 Compound A Fluceto-
Visual Weed Control (%) - 21 DAA Benzyl Ester sulfuron BRAPP CYPIR
SCPJU gae/ha gai/ha Obs Exp Obs Exp Obs Exp 4.38 0 50 -- 50 -- 40
-- 0 0.05 0 -- 0 -- 95 -- 0 0.1 0 -- 0 -- 50 -- 0 0.2 0 -- 20 -- 30
-- 4.38 0.5 65 50 90 50 100 97 4.38 0.1 70 50 100 50 99 70 4.38 0.2
75 50 99 60 100 58 Visual Weed Control Compound A (%) - 22 DAA
Benzyl Ester Flucetosulfuron LEFCH gae/ha gai/ha Obs Exp 8 0 0 --
16 0 20 -- 32 0 15 -- 0 1.7 0 -- 0 5 0 -- 8 1.7 20 0 16 1.7 10 20
32 1.7 10 15 8 5 0 0 16 5 20 20 32 5 30 15 Visual Weed Control
Compound A (%) - 22 DAA Benzyl Ester Flucetosulfuron BRAPP gae/ha
gai/ha Obs Exp 8 0 50 -- 16 0 90 -- 32 0 85 -- 0 1.7 0 -- 8 1.7 75
50 16 1.7 85 90 32 1.7 85 85
TABLE-US-00013 TABLE 13 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Foramsulfuron Herbicidal Compositions
for Control of Weeds Common to Rice. Visual Weed Compound A Control
(%) - 21 DAA Benzyl Ester Foramsulfuron LEFCH gae/ha gai/ha Obs Exp
8 0 20 -- 0 20 0 -- 0 40 25 -- 8 20 30 20 8 40 45 40
TABLE-US-00014 TABLE 14 Synergistic Activity of Foliar-Applied
Compound A Acid and Imazosulfuron Herbicidal Compositions on Weed
Control in a Rice Cropping System. Visual Weed Compound A Control
(%) - 24 DAA Acid Imazosulfuron DIGSA gae/ha gai/ha Obs Exp 17.5 0
25 -- 0 21 0 -- 0 42 0 -- 17.5 21 40 25 17.5 42 50 25
TABLE-US-00015 TABLE 15 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Imazosulfuron Herbicidal Compositions
on Weed Control in a Rice Cropping System. Visual Weed Control
Compound A (%) - 24 DAA Benzyl Ester Imazosulfuron LEFCH gae/ha
gai/ha Obs Exp 8.75 0 0 -- 17.5 0 10 -- 0 21 0 -- 0 42 0 -- 0 84 0
-- 8.75 21 15 0 17.5 21 25 10 8.75 42 10 0 17.5 42 25 10 8.75 84 10
0 17.5 84 25 10
TABLE-US-00016 TABLE 16 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Iodosulfuron-Methyl-Sodium Herbicidal
Compositions on Weed Control in a Rice Cropping System. Visual Weed
Control Compound A Iodosulfuron- (%) - 21 DAA Benzyl Ester methyl
sodium IPOHE gae/ha gai/ha Obs Exp 8 0 10 -- 16 0 10 -- 32 0 45 --
0 2.5 90 -- 0 5 95 -- 8 2.5 95 91 16 2.5 95 91 32 2.5 95 95 8 5 95
96 16 5 99 96 32 5 99 97
TABLE-US-00017 TABLE 17 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Metsulfuronmethyl Herbicidal
Compositions on Weed Control in a Rice Cropping System. Visual Weed
Control Compound A Metsulfuron- (%) - 20 DAA Benzyl Ester methyl
BRAPP gae/ha gai/ha Obs Exp 4.38 0 60 -- 8.75 0 75 -- 17.5 0 85 --
0 7.5 0 -- 0 15 20 -- 4.38 7.5 90 60 8.75 7.5 90 75 17.5 7.5 90 85
4.38 15 95 68 8.75 15 95 80 17.5 15 95 88
TABLE-US-00018 TABLE 18 Synergistic Activity of Foliar-Applied
Compound A Acid and Nicosulfuron Herbicidal Compositions on Control
of Weeds Common to Rice Cropping Systems. Compound A Visual Weed
Control Acid Nicosulfuron (%) - 20 DAA gae/ha gai/ha Obs Exp DIGSA
5.3 0 10 -- 0 8.75 30 -- 0 17.5 55 -- 5.3 8.75 50 37 5.3 17.5 85 60
LEFCH 5.3 0 0 -- 10.6 0 10 -- 21.2 0 15 -- 0 35 75 -- 5.3 35 95 75
10.6 35 70 78 21.2 35 95 79 CYPES 5.3 0 0 -- 0 8.75 10 -- 0 17.5 60
-- 0 35 70 -- 5.3 8.75 85 10 5.3 17.5 85 60 5.3 35 90 70
TABLE-US-00019 TABLE 19 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Nicosulfuron Herbicidal Compositions on
Control of Weeds Common to Rice Cropping Systems. Visual Weed
Control Compound A (%) - 20 DAA Benzyl Ester Nicosulfuron CYPIR
gae/ha gai/ha Obs Exp 4.38 0 15 -- 8.75 0 60 -- 17.5 0 90 -- 0 8.75
80 -- 4.38 8.75 100 83 8.75 8.75 95 92 17.5 8.75 100 98
TABLE-US-00020 TABLE 20 Synergistic Activity of Foliar-Applied
Compound A Acid and Orthosulfamuron Herbicidal Compositions on Weed
Control in a Rice Cropping System. Compound A Visual Weed Acid
Orthosulfamuron Control (%) - 20 DAA gae/ha gai/ha Obs Exp LEFCH
4.38 0 0 -- 8.75 0 0 -- 17.5 0 10 -- 0 7.5 0 -- 0 15 0 -- 4.38 7.5
25 0 8.75 7.5 20 0 17.5 7.5 25 10 4.38 15 15 0 8.75 15 10 0 17.5 15
20 10 CYPES 4.38 0 30 -- 8.75 0 70 -- 0 7.5 0 -- 0 15 30 -- 4.38
7.5 85 30 8.75 7.5 95 70 4.38 15 60 51 8.75 15 95 79
TABLE-US-00021 TABLE 21 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Orthosulfamuron Herbicidal Compositions
on Weed Control in a Rice Cropping System. Visual Weed Compound A
Control (%) - 20 DAA Benzyl Ester Orthosulfamuron LEFCH gae/ha
gai/ha Obs Exp 4.38 0 0 -- 8.75 0 20 -- 17.5 0 40 -- 0 7.5 0 -- 0
15 0 -- 4.38 7.5 30 0 8.75 7.5 25 20 17.5 7.5 45 40 4.38 15 20 0
8.75 15 30 20 17.5 15 55 40 Compound A Visual Weed Control (%) - 20
DAA Benzyl Ester Orthosulfamuron BRAPP CYPES gae/ha gai/ha Obs Exp
Obs Exp 4.38 0 40 -- 70 -- 8.75 0 70 -- 80 -- 0 7.5 0 -- 0 -- 0 15
30 -- 30 -- 4.38 7.5 60 40 90 70 8.75 7.5 85 70 100 80 4.38 15 70
58 90 79 8.75 15 70 79 90 86 Visual Weed Compound A Control (%) -
20 DAA Benzyl Ester Orthosulfamuron CYPIR gae/ha gai/ha Obs Exp
4.38 0 15 -- 0 7.5 50 -- 0 15 75 -- 0 30 65 -- 4.38 7.5 95 58 4.38
15 95 79 4.38 30 95 70
TABLE-US-00022 TABLE 22 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Primisulfuron-methyl Herbicidal
Compositions on Weed Control in a Rice Cropping System Visual Weed
Control Compound A Primisulfuron- (%) - 21 DAA Benzyl Ester methyl
LEFCH gae/ha gai/ha Obs Exp 8 0 25 -- 0 15 40 -- 0 30 60 -- 8 15 70
55 8 30 75 70
TABLE-US-00023 TABLE 23 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Propyrisulfuron Herbicidal Compositions
on Weed Control in a Rice Cropping System Visual Weed Compound A
Control (%) - 21 DAA Benzyl Ester Propyrisulfuron BRAPP gae/ha
gai/ha Obs Exp 4.38 0 50 -- 0 11.25 0 -- 0 22.5 20 -- 0 45 10 --
4.38 11.25 70 50 4.38 22.5 70 60 4.38 45 70 55
TABLE-US-00024 TABLE 24 Synergistic Activity of Foliar-Applied
Compound A Acid and Rimsulfuron Herbicidal Compositions on Control
of Weeds Common to Rice Cropping Systems. Compound A Visual Weed
Control Acid Rimsulfuron (%) - 20 DAA gae/ha gai/ha Obs Exp IPOHE
5.3 0 0 -- 10.6 0 15 -- 21.2 0 25 -- 0 4.38 60 -- 0 8.75 75 -- 5.3
4.38 80 60 10.6 4.38 85 66 21.2 4.38 85 70 5.3 8.75 90 75 10.6 8.75
85 79 21.2 8.75 90 81 CYPES 5.3 0 0 -- 0 2.19 0 -- 0 4.38 0 -- 0
8.75 60 -- 5.3 2.19 30 0 5.3 4.38 90 0 5.3 8.75 85 60
TABLE-US-00025 TABLE 25 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Rimsulfuron Herbicidal Compositions on
Control of Weeds Common to Rice Cropping Systems. Compound A Visual
Weed Control Benzyl Ester Rimsulfuron (%) - 20 DAA gae/ha gai/ha
Obs Exp DIGSA 4.38 0 20 -- 8.75 0 15 -- 17.5 0 20 -- 0 8.75 70 --
4.38 8.75 90 76 8.75 8.75 65 75 17.5 8.75 90 76 IPOHE 4.38 0 10 --
8.75 0 10 -- 17.5 0 25 -- 0 4.38 60 -- 0 8.75 75 -- 4.38 4.38 80 64
8.75 4.38 95 64 17.5 4.38 85 70 4.38 8.75 100 78 8.75 8.75 75 78
17.5 8.75 99 81 CYPES 4.38 0 85 -- 8.75 0 90 -- 17.5 0 90 -- 0 2.19
0 -- 0 4.38 0 -- 4.38 2.19 95 85 8.75 2.19 95 90 17.5 2.19 85 90
4.38 4.38 100 85 8.75 4.38 100 90 17.5 4.38 100 90
TABLE-US-00026 TABLE 26 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Sulfometuron-methyl Herbicidal
Compositions on Control of Weeds Common to Rice Cropping Systems.
Visual Weed Control Compound A Sulfometuron- (%) - 22 DAA Benzyl
Ester methyl DIGSA gae/ha gai/ha Obs Exp 8 0 20 -- 16 0 20 -- 32 0
35 -- 0 35 85 -- 8 35 95 88 16 35 100 88 32 35 90 90
TABLE-US-00027 TABLE 27 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Trifloxysulfuron-sodium Herbicidal
Compositions on Control of Weeds Common to Rice Cropping Systems.
Visual Weed Compound A Trifloxysulfuron- Control (%) - 21 DAA
Benzyl Ester sodium DIGSA gae/ha gai/ha Obs Exp 8 0 25 -- 16 0 30
-- 32 0 50 -- 0 24 65 -- 8 24 85 74 16 24 99 76 32 24 95 83
TABLE-US-00028 BRAPP Brachiaria platyphylla (Griseb.) signalgrass,
broadleaf Nash CYPDI Cyperus difformis L. sedge, smallflower
umbrella CYPES Cyperus esculentus L. nutsedge, yellow CYPIR Cyperus
iria L. flatsedge, rice DIGSA Digitaria sanguinalis (L.) Scop.
crabgrass, large ECHCG Echinochloa crusgalli (L.) Beauv.
barnyardgrass ECHCO Echinochloa colona (L.) Link junglerice IPOHE
Ipomoea hederacea Jacq. morningglory, ivyleaf ISCRU Ischaemum
rugosum Salisb. saramollagrass LEFCH Leptochloa chinensis (L.) Nees
sprangletop, Chinese SCPJU Schoenoplectus juncoides (Roxb.)
bulrush, Japanese Palla gae/ha = grams acid equivalent per hectare
gai/ha = grams active ingredient per hectare Obs = observed value
Exp = expected value as calculated by Colby's equation DAA = days
after application
Example II
Evaluation of in-Water Applied Herbicidal Mixtures for Weed Control
in Transplanted Paddy Rice
[0266] Weed seeds or nutlets of the desired test plant species were
planted in puddled soil (mud) prepared by mixing a shredded,
non-sterilized mineral soil (50.5 percent silt, 25.5 percent clay,
and 24 percent sand, with a pH of about 7.6 and an organic matter
content of about 2.9 percent) and water at a 1:1 volumetric ratio.
The prepared mud was dispensed in 365 mL aliquots into 16-ounce
(oz.) non-perforated plastic pots with a surface area of 86.59
square centimeters (cm.sup.2) leaving a headspace of 3 centimeters
(cm) in each pot. Rice seeds were planted in Sun Gro MetroMix.RTM.
306 planting mixture, which typically has a pH of 6.0 to 6.8 and an
organic matter content of about 30 percent, in plastic plug trays.
Seedlings at the second or third leaf stage of growth were
transplanted into 860 mL of mud contained in 32-oz. non-perforated
plastic pots with a surface area of 86.59 cm.sup.2 4 days prior to
herbicide application. The paddy was created by filling the
headspace of the pots with 2.5 to 3 cm of water. When required to
ensure good germination and healthy plants, a fungicide treatment
and/or other chemical or physical treatment was applied. The plants
were grown for 4-22 days in a greenhouse with an approximate 14 h
photoperiod which was maintained at about 29'C during the day and
26.degree. C. during the night. Nutrients were added as
Osmocote.RTM. (19:6:12, N:P:K+minor nutrients) at 2 g per 16-oz.
pot and 4 g per 32-oz. pot. Water was added on a regular basis to
maintain the paddy flood, and supplemental lighting was provided
with overhead metal halide 1000-Watt lamps as necessary. The plants
were employed for testing when they reached the first through
fourth true leaf stage.
[0267] Treatments consisted of the acid or esters of
4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine--
2-carboxylic acid (compound A) each formulated as an SC and various
herbicidal components alone and in combination. Forms of compound A
were applied on an acid equivalent basis.
Forms of compound A (compound of formula I) tested include:
##STR00038##
[0268] Other herbicidal components were applied on an active
ingredient basis and included acetolactate synthase
(ALS)-inhibiting herbicides (sulfonylurea chemical class),
azimsulfuron formulated as Gulliver.RTM., bensulfuron-methyl
formulated as Londax.RTM. 60DF, cyclosulfamuron (technical grade
materail), ethoxysulfuron formulated as Sunrice.RTM. 15 WDG,
flucetosulfuron formulated as Sukedachi.RTM. 1KG G, imazosulfuron
formulated as Brazzos.RTM., metsulfuron-methyl formulated as
Lorate.RTM., nicosulfuron formulated as Accent.RTM.,
orthosulfamuron formulated as Strada.RTM. WG, propyrisulfuron
formulated as Zeta One.RTM., and rimsulfuron formulated as
Matrix.RTM. WG.
[0269] Treatment requirements for each compound or herbicidal
component were calculated based upon the rates being tested, the
concentration of active ingredient or acid equivalent in the
formulation, an application volume of 2 mL per component per pot,
and an application area of 86.59 cm.sup.2 per pot.
[0270] For formulated compounds, a measured amount was placed in an
individual 100 or 200 mL glass vial and was dissolved in a volume
of 1.25% (v/v) Agri-Dex.RTM. crop oil concentrate to obtain
application solutions. If the test compound did not dissolve
readily, the mixture was warmed and/or sonicated.
[0271] For technical grade compounds, a weighed amount was placed
in an individual 100 to 200 mL glass vial and was dissolved in a
volume of acetone to obtain concentrated stock solutions. If the
test compound did not dissolve readily, the mixture was warmed
and/or sonicated. The concentrated stock solutions obtained were
diluted with an equivalent volume of an aqueous mixture containing
2.5% (v/v) crop oil concentrate so that the final application
solutions contained 1.25% (v/v) crop oil concentrate.
[0272] Applications were made by injecting with a pipetter
appropriate amounts of the application solutions, individually and
sequentially, into the aqueous layer of the paddy. Control plants
were treated in the same manner with the solvent blank.
Applications were made so that all treated plant material received
the same concentrations of acetone and crop oil concentrate.
[0273] The treated plants and control plants were placed in a
greenhouse as described above and water was added as needed to
maintain a paddy flood. After approximately 3 weeks the condition
of the test plants as compared with that of the untreated plants
was determined visually and scored on a scale of 0 to 100 percent
where 0 corresponds to no injury or growth inhibition and 100
corresponds to complete kill.
[0274] Colby's equation was used to determine the herbicidal
effects expected from the mixtures (Colby, S. R. 1967. Calculation
of the synergistic and antagonistic response of herbicide
combinations. Weeds 15:20-22.).
[0275] The following equation was used to calculate the expected
activity of mixtures containing two active ingredients, A and
B:
Expected=A+B-(A.times.B/100)
[0276] A=observed efficacy of active ingredient A at the same
concentration as used in the mixture.
[0277] B=observed efficacy of active ingredient B at the same
concentration as used in the mixture.
[0278] Some of the compounds tested, application rates employed,
plant species tested, and results are given in Tables 28-50.
TABLE-US-00029 TABLE 28 Synergistic Activity of In-Water
Applications of Compound A Acid and Azimsulfuron Herbicidal
Compositions on Weed Control in a Rice Cropping System. Compound A
Visual Weed Control (%) - 20 DAA Acid Azimsulfuron ECHOR SCPMA
gae/ha gai/ha Obs Exp Obs Exp 8.75 0 20 -- 40 -- 17.5 0 30 -- 20 --
35 0 40 -- 20 -- 0 2.5 0 -- 70 -- 8.75 2.5 40 20 95 82 17.5 2.5 60
30 100 76 35 2.5 60 40 100 76 35 0 25 -- 0 -- 70 0 35 -- 0 -- 0 25
60 -- 85 -- 35 25 80 70 98 85 70 25 100 74 98 85
TABLE-US-00030 TABLE 29 Synergistic Activity of In-Water
Applications of Compound A Benzyl Ester and Azimsulfuron Herbicidal
Compositions on Weed Control in a Rice Cropping System. Compound A
Visual Weed Control Benzyl Ester Azimsulfuron (%) - 20 DAA gae/ha
gai/ha Obs Exp ECHOR 4.38 0 10 -- 8.75 0 20 -- 17.5 0 30 -- 0 2.5 0
-- 0 5 20 -- 4.38 2.5 40 10 8.75 2.5 40 20 17.5 2.5 60 30 4.38 5 30
28 8.75 5 40 36 17.5 5 70 44 SCPMA 4.38 0 10 -- 8.75 0 0 -- 17.5 0
20 -- 0 2.5 70 -- 4.38 2.5 80 73 8.75 2.5 80 70 17.5 2.5 90 76
Compound A Visual Weed Control (%) - 20 DAA Benzyl Ester
Azimsulfuron ECHOR SCPMA gae/ha gai/ha Obs Exp Obs Exp 35 0 53 -- 0
-- 70 0 73 -- 0 -- 0 25 60 -- 85 -- 35 25 88 81 90 85 70 25 100 89
100 85
TABLE-US-00031 TABLE 30 Synergistic Activity of In-Water
Applications of Compound A n-Butyl Ester and Azimsulfuron
Herbicidal Compositions on Weed Control in a Rice Cropping System.
Visual Weed Control Compound A (%) - 20 DAA n-Butyl Ester
Azimsulfuron ECHOR gae/ha gai/ha Obs Exp 35 0 28 -- 70 0 45 -- 0 25
60 -- 35 25 75 71 70 25 93 78
TABLE-US-00032 TABLE 31 Synergistic Activity of In-Water
Applications of Compound A Acid and Bensulfuron-Methyl Herbicidal
Compositions on Weed Control in a Rice Cropping System. Visual Weed
Compound A Bensulfuron- Control (%) - 25 DAA Acid methyl ECHOR
gae/ha gai/ha Obs Exp 8.75 0 0 -- 17.5 0 0 -- 35 0 40 -- 0 35 80 --
0 70 85 -- 8.75 35 95 80 17.5 35 95 80 35 35 100 88 8.75 70 100 85
17.5 70 100 85 35 70 95 91 Compound A Bensulfuron- Visual Weed
Control (%) - 19 DAA Acid methyl ECHOR LEFCH gae/ha gai/ha Obs Exp
Obs Exp 42 0 15 -- 10 -- 0 70 78 -- 23 -- 42 70 99 81 43 30
TABLE-US-00033 TABLE 32 Synergistic Activity of In-Water
Applications of Compound A Benzyl Ester and Bensulfuron-Methyl
Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound A Bensulfuron- Visual Weed Control Benzyl Ester methyl (%)
- 21 DAA gae/ha gai/ha Obs Exp ECHOR 8 0 8 -- 16 0 5 -- 0 35 0 -- 0
70 15 -- 8 35 30 8 16 35 20 5 8 70 35 21 16 70 20 19 SCPMA 48 0 0
-- 96 0 0 -- 0 17.5 45 -- 0 35 90 -- 48 17.5 85 45 96 17.5 100 45
48 35 99 90 96 35 95 90
TABLE-US-00034 TABLE 33 Synergistic Activity of In-Water
Applications of Compound A Benzyl Ester and Cyclosulfamuron
Herbicidal Compositions on Weed Control in a Rice Cropping System.
Visual Weed Compound A Control (%) - 21 DAA Benzyl Ester
Cyclosulfamuron SCPMA gae/ha gai/ha Obs Exp 8 0 0 -- 16 0 0 -- 32 0
0 -- 0 12.5 75 -- 8 12.5 85 75 16 12.5 90 75 32 12.5 90 75
TABLE-US-00035 TABLE 34 Synergistic Activity of In-Water
Applications of Compound A Acid and Ethoxysulfuron Herbicidal
Compositions on Weed Control in a Rice Cropping System. Compound A
Visual Weed Control Acid Ethoxysulfuron (%) - 22 DAA gae/ha gai/ha
Obs Exp ECHOR 10.6 0 15 -- 21.2 0 30 -- 42.4 0 40 -- 0 7.5 10 --
10.6 7.5 55 24 21.2 7.5 40 37 42.4 7.5 85 46 LEFCH 10.6 0 20 --
21.2 0 40 -- 42.4 0 60 -- 0 15 0 -- 10.6 15 20 20 21.2 15 50 40
42.4 15 100 60
TABLE-US-00036 TABLE 35 Synergistic Activity of In-Water
Applications of Compound A Benzyl Ester and Ethoxysulfuron
Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound A Visual Weed Control Benzyl Ester Ethoxysulfuron (%) - 22
DAA gae/ha gai/ha Obs Exp ECHOR 17.5 0 30 -- 0 7.5 10 -- 0 15 20 --
17.5 7.5 99 37 17.5 15 85 44 LEFCH 4.38 0 20 -- 0 7.5 0 -- 0 15 0
-- 4.38 7.5 30 20 4.38 15 70 20
TABLE-US-00037 TABLE 36 Synergistic Activity of In-Water
Applications of Compound A Acid and Flucetosulfuron Herbicidal
Compositions on Weed Control in a Rice Cropping System. Compound A
Visual Weed Control Acid Flucetosulfuron (%) - 21 DAA gae/ha gai/ha
Obs Exp ECHOR 8.75 0 10 -- 17.5 0 10 -- 35 0 15 -- 0 0.1 0 -- 0 0.2
0 -- 8.75 0.1 20 10 17.5 0.1 25 10 35 0.1 40 15 8.75 0.2 30 10 17.5
0.2 40 10 35 0.2 40 15 LEFCH 17.5 0 20 -- 0 0.1 0 -- 0 0.2 0 --
17.5 0.1 50 20 17.5 0.2 50 20
TABLE-US-00038 TABLE 37 Synergistic Activity of In-Water
Applications of Compound A Benzyl Ester and Flucetosulfuron
Herbicidal Compositions on Weed Control in a Rice Cropping System.
Visual Weed Control Compound A (%) - 21 DAA Benzyl Ester
Flucetosulfuron ECHOR gae/ha gai/ha Obs Exp 8.75 0 25 -- 17.5 0 25
-- 0 0.1 0 -- 0 0.2 0 -- 8.75 0.1 70 25 17.5 0.1 95 25 8.75 0.2 30
25 17.5 0.2 95 25
TABLE-US-00039 TABLE 38 Synergistic Activity of In-Water
Applications of Compound A Acid and Imazosulfuron Herbicidal
Compositions on Weed Control in a Rice Cropping System. Compound A
Acid Imazosulfuron gae/ha gai/ha Obs Exp Visual Weed Control (%) -
21 DAA ECHCO 8.75 0 0 -- 17.5 0 20 -- 0 22.5 20 -- 0 45 20 -- 8.75
22.5 30 20 17.5 22.5 65 36 8.75 45 55 20 17.5 45 50 36 Visual Weed
Control (%) - 20 DAA SCPMA 35 0 0 -- 70 0 0 -- 0 168 65 -- 35 168
90 65 70 168 100 65
TABLE-US-00040 TABLE 39 Synergistic Activity of In-Water
Applications of Compound A Benzyl Ester and Imazosulfuron
Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound A Benzyl Ester Imazosulfuron gae/ha gai/ha Obs Exp Visual
Weed Control (%) - 21 DAA ECHCO 4.38 0 45 -- 8.75 0 30 -- 17.5 0 95
-- 0 45 20 -- 4.38 45 70 56 8.75 45 70 44 17.5 45 95 96 Visual Weed
Control (%) - 20 DAA SCPMA 35 0 0 -- 70 0 0 -- 0 168 65 -- 35 168
95 65 70 168 100 65
TABLE-US-00041 TABLE 40 Synergistic Activity of In-Water
Applications of Compound A n-Butyl Ester and Imazosulfuron
Herbicidal Compositions on Weed Control in a Rice Cropping System.
Visual Weed Control Compound A (%) - 20 DAA n-Butyl Ester
Imazosulfuron SCPMA gae/ha gai/ha Obs Exp 35 0 0 -- 70 0 0 -- 0 168
65 -- 35 168 95 65 70 168 95 65
TABLE-US-00042 TABLE 41 Synergistic Activity of In-Water
Applications of Compound A Acid and Metsulfuron-methyl Herbicidal
Compositions on Weed Control in a Rice Cropping System. Visual Weed
Control Compound A Metsulfuron- (%) - 21 DAA Acid methyl ECHOR
gae/ha gai/ha Obs Exp 10.6 0 0 -- 21.2 0 15 -- 42.4 0 15 -- 0 7.5
50 -- 0 15 65 -- 10.6 7.5 85 50 21.2 7.5 80 58 42.4 7.5 85 58 10.6
15 90 65 21.2 15 85 70 42.4 15 99 70
TABLE-US-00043 TABLE 42 Synergistic Activity of In-Water
Applications of Compound A Benzyl Ester and Metsulfuron-methyl
Herbicidal Compositions on Weed Control in a Rice Cropping System.
Visual Weed Control Compound A Metsulfuron- (%) - 21 DAA Benzyl
Ester methyl ECHOR gae/ha gai/ha Obs Exp 4.38 0 15 -- 8.75 0 15 --
17.5 0 20 -- 0 7.5 50 -- 0 15 65 -- 4.38 7.5 80 58 8.75 7.5 90 58
17.5 7.5 85 60 4.38 15 90 70 8.75 15 99 70 17.5 15 100 72
TABLE-US-00044 TABLE 43 Synergistic Activity of In-Water
Applications of Compound A Acid and Nicosulfuron Herbicidal
Compositions on Control of Weeds Common to Rice Cropping Systems.
Visual Weed Compound A Control (%) - 20 DAA Acid Nicosulfuron ECHOR
LEFCH gae/ha gai/ha Obs Exp Obs Exp 10.6 0 10 -- 30 -- 21.2 0 30 --
20 -- 42.4 0 45 -- 75 -- 0 17.5 0 -- 60 -- 10.6 17.5 50 10 90 72
21.2 17.5 40 30 100 68 42.4 17.5 65 45 100 90 Visual Weed Control
(%) - 20 Compound A DAA Acid Nicosulfuron CYPRO gae/ha gai/ha Obs
Exp 10.6 0 10 -- 21.2 0 20 -- 0 17.5 30 -- 0 35 70 -- 10.6 17.5 50
37 21.2 17.5 70 44 10.6 35 99 73 21.2 35 95 76
TABLE-US-00045 TABLE 44 Synergistic Activity of In-Water
Applications of Compound A Benzyl Ester and Nicosulfuron Herbicidal
Compositions on Control of Weeds Common to Rice Cropping Systems.
Visual Weed Control (%) - 20 Compound A DAA Benzyl Ester
Nicosulfuron ECHOR gae/ha gai/ha Obs Exp 8.75 0 20 -- 17.5 0 30 --
0 17.5 0 -- 0 35 50 -- 8.75 17.5 30 20 17.5 17.5 85 30 8.75 35 90
60 17.5 35 85 65
TABLE-US-00046 TABLE 45 Synergistic Activity of In-Water
Applications of Compound A Acid and Orthosulfamuron Herbicidal
Compositions on Weed Control in a Rice Cropping System. Visual Weed
Control (%) - 20 Compound A DAA Acid Orthosulfamuron SCPMA gae/ha
gai/ha Obs Exp 42.4 0 0 -- 84.8 0 0 -- 0 60 85 -- 42.4 60 95 85
84.8 60 100 85
TABLE-US-00047 TABLE 46 Synergistic Activity of In-Water
Applications of Compound A Benzyl Ester and Orthosulfamuron
Herbicidal Compositions on Weed Control in a Rice Cropping System.
Visual Weed Control (%) - 20 Compound A DAA Benzyl Ester
Orthosulfamuron SCPMA gae/ha gai/ha Obs Exp 35 0 0 -- 70 0 0 -- 0
60 85 -- 35 60 98 85 70 60 95 85 Visual Weed Control (%) - 21
Compound A DAA Benzyl Ester Orthosulfamuron ECHOR gae/ha gai/ha Obs
Exp 4.38 0 0 -- 8.75 0 10 -- 17.5 0 60 -- 0 15 10 -- 4.38 15 25 10
8.75 15 25 19 17.5 15 85 64
TABLE-US-00048 TABLE 47 Synergistic Activity of In-Water
Applications of Compound A Acid and Propyrisulfuron Herbicidal
Compositions on Weed Control in a Rice Cropping System. Visual Weed
Control (%) - 21 Compound A DAA Acid Propyrisulfuron LEFCH gae/ha
gai/ha Obs Exp 8.75 0 0 -- 17.5 0 20 -- 0 22.5 0 -- 0 45 0 -- 8.75
22.5 30 0 17.5 22.5 50 20 8.75 45 100 0 17.5 45 30 20
TABLE-US-00049 TABLE 48 Synergistic Activity of In-Water
Applications of Compound A Benzyl Ester and Propyrisulfuron
Herbicidal Compositions on Weed Control in a Rice Cropping System.
Visual Weed Control (%) - 21 Compound A DAA Benzyl Ester
Propyrisulfuron FIMMI gae/ha gai/ha Obs Exp 8 0 15 -- 16 0 65 -- 32
0 75 -- 0 11.25 85 -- 0 22.5 88 -- 0 45 95 -- 8 11.25 100 87 16
11.25 100 95 32 11.25 100 96 8 22.5 100 89 16 22.5 100 96 32 22.5
100 97 8 45 100 96 16 45 100 98 32 45 100 99 Visual Weed Control
(%) - 21 Compound A DAA Benzyl Ester Propyrisulfuron SCPMA gae/ha
gai/ha Obs Exp 8 0 0 -- 16 0 0 -- 32 0 0 -- 0 11.25 80 -- 8 11.25
95 80 16 11.25 85 80 32 11.25 100 80
TABLE-US-00050 TABLE 49 Synergistic Activity of In-Water
Applications of Compound A Acid and Rimsulfuron Herbicidal
Compositions on Control of Weeds Common to Rice Cropping Systems.
Visual Weed Compound A Control (%) - 20 DAA Acid Rimsulfuron LEFCH
CYPRO gae/ha gai/ha Obs Exp Obs Exp 10.6 0 30 -- 10 -- 21.2 0 20 --
20 -- 42.4 0 75 -- 95 -- 0 4.38 0 -- 0 -- 10.6 4.38 50 30 100 10
21.2 4.38 50 20 90 20 42.4 4.38 90 75 99 95
TABLE-US-00051 TABLE 50 Synergistic Activity of In-Water
Applications of Compound A Benzyl Ester and Rimsulfuron Herbicidal
Compositions on Control of Weeds Common to Rice Cropping Systems.
Visual Weed Control (%) - 20 Compound A DAA Benzyl Ester
Rimsulfuron ECHCG gae/ha gai/ha Obs Exp 4.38 0 15 -- 8.75 0 20 --
17.5 0 40 -- 0 4.38 0 -- 0 8.75 0 -- 4.38 4.38 20 15 8.75 4.38 35
20 17.5 4.38 25 40 4.38 8.75 30 15 8.75 8.75 25 20 17.5 8.75 95 40
Visual Weed Control (%) - 20 Compound A DAA Benzyl Ester
Rimsulfuron LEFCH gae/ha gai/ha Obs Exp 4.38 0 20 -- 0 4.38 0 -- 0
8.75 30 -- 4.38 4.38 70 20 4.38 8.75 100 44 Visual Weed Control (%)
- 20 Compound A DAA Benzyl Ester Rimsulfuron CYPRO gae/ha gai/ha
Obs Exp 4.38 0 50 -- 8.75 0 0 -- 17.5 0 90 -- 0 4.38 0 -- 4.38 4.38
90 50 8.75 4.38 90 0 17.5 4.38 85 90
TABLE-US-00052 CYPRO Cyperus rotundus L. nutsedge, purple ECHCG
Echinochloa crusgalli (L.) Beauv. barnyardgrass ECHCO Echinochloa
colona (L.) Link junglerice ECHOR Echinochloa oryzoides (Ard.)
Fritsch watergrass, early FIMMI Fimbristylis miliacea (L.) Vahl
fringerush, globe LEFCH Leptochloa chinensis (L.) Nees sprangletop,
Chinese SCPMA Schoenoplectus maritimus (L.) Lye clubrush, sea
gae/ha = grams acid equivalent per hectare gai/ha = grams active
ingredient per hectare Obs = observed value Exp = expected value as
calculated by Colby's equation DAA = days after application
Example III
Evaluation of Post-Emergence Foliar-Applied Herbicidal Mixtures for
Weed Control in Cereal Crops in the Greenhouse
[0279] Seeds of the desired test plant species were planted in Sun
Gro MetroMix.RTM. 306 planting mixture, which typically has a pH of
6.0 to 6.8 and an organic matter content of about 30 percent, in
plastic pots with a surface area of 103.2 square centimeters
(cm.sup.2). When required to ensure good germination and healthy
plants, a fungicide treatment and/or other chemical or physical
treatment was applied. The plants were grown for 7-36 days in a
greenhouse with an approximate 14 hour photoperiod which was
maintained at about 18.degree. C. during the day and 17.degree. C.
during the night. Nutrients and water were added on a regular basis
and supplemental lighting was provided with overhead metal halide
1000-Watt lamps as necessary. The plants were employed for testing
when they reached the second or third true leaf stage.
[0280] Treatments consisted of the benzyl ester of
4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine--
2-carboxylic acid (Compound A), formulated as an SC (suspension
concentrate), and a second cereal herbicide alone and in
combination.
Forms of compound A (compound of formula I) tested include:
##STR00039##
[0281] Measured aliquot of benzyl ester of
4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine--
2-carboxylic acid (Compound A) was placed in 25 milliliter (mL)
glass vials and diluted in a volume of 1.25% (v/v) Agri-dex crop
oil concentrated to obtain stock solutions. Compound requirements
are based upon a 12 mL application volume at a rate of 187 liters
per hectare (L/ha). Spray solutions of the second cereal herbicide
and experimental compound mixtures were prepared by adding the
stock solutions to the appropriate amount of dilution solution to
form 12 mL spray solution with active ingredients in two- and
three-way combinations. Formulated compounds were applied to the
plant material with an overhead Mandel track sprayer equipped with
an 8002E nozzle calibrated to deliver 187 L/ha over an application
area of 0.503 square meters (m.sup.2) at a spray height of 18
inches (46 cm) above average plant canopy. Control plants were
sprayed in the same manner with the solvent blank.
[0282] The treated plants and control plants were placed in a
greenhouse as described above and watered by sub-irrigation to
prevent wash-off of the test compounds. After 20-22 days, the
condition of the test plants as compared with that of the control
plants was determined visually and scored on a scale of 0 to 100
percent where 0 corresponds to no injury and 100 corresponds to
complete kill.
[0283] Colby's equation was used to determine the herbicidal
effects expected from the mixtures (Colby, S. R. 1967. Calculation
of the synergistic and antagonistic response of herbicide
combinations. Weeds 15:20-22.).
[0284] The following equation was used to calculate the expected
activity of mixtures containing two active ingredients, A and
B:
Expected=A+B-(A.times.B/100)
[0285] A=observed efficacy of active ingredient A at the same
concentration as used in the mixture.
[0286] B=observed efficacy of active ingredient B at the same
concentration as used in the mixture.
The compounds tested, application rates employed, plant species
tested, and results are given in Tables 51-57.
TABLE-US-00053 TABLE 51 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Amidosulfuron Herbicidal Compositions
on Weed Control in a Cereal Cropping System. Application Rate
(gai/ha) Compound A Amido- GALAP LAMPU VERPE Benzyl Ester sulfuron
Obs Exp Obs Exp Obs Exp 8.75 0 70 -- 83 -- 50 -- 0 10 48 -- 0 -- 0
-- 8.75 10 93 84 89 83 65 50
TABLE-US-00054 TABLE 52 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Chlorsulfuron Herbicidal Compositions
on Weed Control in a Cereal Cropping System. Application Rate
(gai/ha) Compound A Benzyl VIOTR CIRAR Ester Chlorsulfuron Obs Exp
Obs Exp 8.75 0 50 -- 40 -- 0 2.2 70 -- 78 -- 8.75 2.2 89 85 96
87
TABLE-US-00055 TABLE 53 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Flupyrsulfuron-methyl sodium Herbicidal
Compositions on Weed Control in a Cereal Cropping System.
Application Rate (gai/ha) Compound A Benzyl Flupyrsulfuron- VERPE
CIRAR Ester methyl sodium Obs Exp Obs Exp 8.75 0 50 -- 40 -- 0 5 0
-- 75 -- 8.75 5 63 50 95 85
TABLE-US-00056 TABLE 54 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Iodosulfuron-methyl sodium Herbicidal
Compositions on Weed Control in a Cereal Cropping System.
Application Rate (gai/ha) Iodo- sulfuron- Compound A methyl VIOTR
MATCH CIRAR Benzyl Ester sodium Obs Exp Obs Exp Obs Exp 8.75 0 50
-- 20 -- 40 -- 0 2.5 82 -- 94 -- 60 -- 8.75 2.5 94 91 100 95 99
76
TABLE-US-00057 TABLE 55 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Mesoulfuron-methyl Herbicidal
Compositions on Weed Control in a Cereal Cropping System.
Application Rate (gai/ha) Mesosul- Compound A furon- VERPE MATCH
CIRAR Benzyl Ester methyl Obs Exp Obs Exp Obs Exp 8.75 0 50 -- 20
-- 40 -- 0 3 5 -- 40 -- 78 -- 8.75 3 68 53 75 52 96 87
TABLE-US-00058 TABLE 56 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Metsulfuron-methyl Herbicidal
Compositions on Weed Control in a Cereal Cropping System.
Application Rate (gai/ha) Compound A Benzyl Metsulfuron- MATCH
CIRAR Ester methyl Obs Exp Obs Exp 8.75 0 20 -- 40 -- 0 1.1 89 --
65 -- 8.75 1.1 96 91 97 79
TABLE-US-00059 TABLE 57 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Sulfosulfuron Herbicidal Compositions
on Weed Control in a Cereal Cropping System. Application Rate
(gai/ha) Compound A Sulfo- LAMPU VERPE MATCH CIRAR Benzyl Ester
sulfuron Obs Exp Obs Exp Obs Exp Obs Exp 8.75 0 83 -- 50 -- 20 --
40 -- 0 8.75 5 -- 35 -- 95 -- 70 -- 8.75 8.75 94 83 75 68 100 96 85
82
TABLE-US-00060 TABLE 58 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Thifensulfuron-methyl Herbicidal
Compositions on Weed Control in a Cereal Cropping System.
Application Rate (gai/ha) Compound A Benzyl Thifensulfuron- CIRAR
Ester methyl Obs Exp 8.75 0 40 -- 0 3.75 35 -- 8.75 3.75 80 61
TABLE-US-00061 TABLE 59 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Tribenuron-methyl Herbicidal
Compositions on Weed Control in a Cereal Cropping System.
Application Rate (gai/ha) Compound A Benzyl Tribenuron- MATCH CIRAR
Ester methyl Obs Exp Obs Exp 8.75 0 20 -- 40 -- 0 2.2 90 -- 50 --
8.75 2.2 95 92 80 70
TABLE-US-00062 GALAP Galium aparine (L.) cleavers MATCH Chamomilla
chamomilla (L.) Rydb. mayweed, scented VERPE Veronica persica Poir.
speedwell, bird's-eye VIOTR Viola tricolor (L.) pansy, wild CIRAR
Cirsium arvense (L.) Scop. thistle, Canada LAMPU Lamium purpureum
(L.) deadnettle, purple
Example IV
Evaluation of Post-Emergence Herbicidal Activity of Mixtures in
Forage Crops In the Greenhouse
[0287] Seeds or root cuttings of the desired test plant species
were planted in Sun Gro MetroMix.RTM. 306 planting mixture, which
typically has a pH of 6.0 to 6.8 and an organic matter content of
about 30 percent, in plastic pots with a surface area of 126.6
square centimeters (cm.sup.2). When required to ensure good
germination and healthy plants, a fungicide treatment and/or other
chemical or physical treatment was applied. The plants were grown
for 14-60 days in a greenhouse with an approximate 14 hour
photoperiod which was maintained at approximately 28.degree. C.
during the day and 24.degree. C. during the night. Nutrients and
water were added on a regular basis and supplemental lighting was
provided with overhead metal halide 1000-Watt lamps as necessary.
The plants were employed for testing when they reached the BBCH13
to BBCH23 leaf stage.
[0288] Treatments consisted of the benzyl ester of
4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine--
2-carboxylic acid (Compound A), formulated as a SC, and a second
herbicide alone and in combination.
Forms of compound A (compound of formula I) tested include:
##STR00040##
[0289] A measured aliquot of Compound A was placed in 25 milliliter
(mL) glass vial and diluted in a volume of 1.25% (v/v) Agri-dex
crop oil concentrated to obtain stock solutions. Compound
requirements are based upon a 12 mL application volume at a rate of
187 liters per hectare (L/ha). Spray solutions of the second cereal
herbicide and experimental compound mixtures were prepared by
adding the stock solutions to the appropriate amount of dilution
solution to form 12 mL spray solution with active ingredients in
two- and three-way combinations. Formulated compounds were applied
to the plant material with an overhead Mandel track sprayer
equipped with an 8002E nozzle calibrated to deliver 187 L/ha over
an application area of 0.503 square meters (m.sup.2) at a spray
height of 18 inches (46 cm) above average plant canopy. Control
plants were sprayed in the same manner with the solvent blank.
[0290] The treated plants and control plants were placed in a
greenhouse as described above and watered by sub-irrigation to
prevent wash-off of the test compounds. After approximately 21
days, the condition of the test plants, as compared with that of
the control plants, was determined visually and scored on a scale
of 0 to 100 percent where 0 corresponds to no injury and 100
corresponds to complete kill.
[0291] Colby's equation was used to determine the herbicidal
effects expected from the mixtures (Colby, S. R. 1967. Calculation
of the synergistic and antagonistic response of herbicide
combinations. Weeds 15:20-22.).
[0292] The following equation was used to calculate the expected
activity of mixtures containing two active ingredients, A and
B:
Expected=A+B-(A.times.B/100)
[0293] A=observed efficacy of active ingredient A at the same
concentration as used in the mixture.
[0294] B=observed efficacy of active ingredient B at the same
concentration as used in the mixture.
Some of the compounds tested, application rates employed, plant
species tested, and results are given in Table 58.
TABLE-US-00063 TABLE 58 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Metsulfuron methyl Ester (ME)
Herbicidal Compositions on Weed Control in a Forage System.
Application Rate (gai/ha) Compound A Metsul- SIDSP CASOB POROL
Benzyl Ester furon ME Obs Exp Obs Exp Obs Exp 2.2 0 77 -- 33 -- 47
-- 4.4 0 85 -- 38 -- 60 -- 0 1.1 52 -- 8 -- 80 -- 2.2 1.1 96 89 50
39 93 89 4.4 1.1 98 93 65 43 95 92
TABLE-US-00064 CASOB Cassia obtusifolia L. sicklepod POROL
Portulaca oleracea L. portulaca SIDSP Sida spinosa L. sida,
prickly
Example V
Evaluation of Pre-Emergence Soil-Applied Herbicidal Mixtures for
Weed Control
[0295] Seeds or nutlets of the desired test plant species were
planted in a soil matrix prepared by mixing a loam soil (32 percent
silt, 23 percent clay, and 45 percent sand, with a pH of about 6.5
and an organic matter content of about 1.9 percent) and calcareous
grit in an 80 to 20 ratio. The soil matrix was contained in plastic
pots with a volume of 1 quart and a surface area of 83.6 square
centimeters (cm.sup.2).
[0296] Treatments consisted of the benzyl ester of
4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine--
2-carboxylic acid (compound A) formulated as an SC (suspension
concentrate) and various herbicidal components alone and in
combination. Forms of compound A were applied on an acid equivalent
basis.
Forms of compound A (compound of formula I) tested include:
##STR00041##
[0297] Other herbicidal components were applied on an acid
equivalent or active ingredient basis and included the acetolactate
synthase (ALS)-inhibiting herbicide, flazasulfuron, formulated as
Katana.RTM..
[0298] Treatment requirements were calculated based upon the rates
being tested, the concentration of active ingredient or acid
equivalent in the formulation, and a 12 mL application volume at a
rate of 187 L/ha.
[0299] For treatments comprised of formulated compounds, measured
amounts of compounds were placed individually in 25 mL glass vials
and diluted in a volume of 1.25% (v/v) Agri-Dex.RTM. crop oil
concentrate (COC) to obtain 12.times. stock solutions. If a test
compound did not dissolve readily, the mixture was warmed and/or
sonicated. Application solutions were prepared by adding an
appropriate amount of each stock solution (e.g., 1 mL) and diluted
to the appropriate final concentrations with the addition of 10 mL
of an aqueous mixture of 1.25% (v/v) COC so that the final spray
solutions contained 1.25% (v/v) COC.
[0300] For treatments comprised of technical compounds, weighed
amounts can be placed individually in 25 mL glass vials and
dissolved in a volume of 97:3 (v/v) acetone/DMSO to obtain
12.times. stock solutions. If a test compound does not dissolve
readily, the mixture can be warmed and/or sonicated. Application
solutions can be prepared by adding an appropriate amount of each
stock solution (e.g., 1 mL) and diluted to the appropriate final
concentrations with the addition of 10 mL of an aqueous mixture of
1.5% (v/v) COC so that the final spray solutions contain 1.25%
(v/v) COC. When technical materials are used, the concentrated
stock solutions can be added to the spray solutions so that the
final acetone and DMSO concentrations of the application solutions
are 16.2% and 0.5%, respectively.
[0301] For treatments comprised of formulated and technical
compounds, weighed amounts of the technical materials can be placed
individually in 25 mL glass vials and dissolved in a volume of 97:3
(v/v) acetone/DMSO to obtain 12.times. stock solutions, and
measured amounts of the formulated compounds can be placed
individually in 25 mL glass vials and diluted in a volume of 1.5%
(v/v) COC or water to obtain 12.times. stock solutions. If a test
compound does not dissolve readily, the mixture can be warmed
and/or sonicated. Application solutions can be prepared by adding
an appropriate amount of each stock solution (e.g., 1 mL) and
diluted to the appropriate final concentrations with the addition
of an appropriate amount of an aqueous mixture of 1.5% (v/v) COC so
that the final spray solutions contain 1.25% (v/v) COC. As
required, additional water and/or 97:3 (v/v) acetone/DMSO can be
added to individual application solutions so that the final acetone
and DMSO concentrations of the application solutions being compared
are 8.1% and 0.25%, respectively.
[0302] All stock solutions and applications solutions were visually
inspected for compound compatibility prior to application. Spray
solutions were applied to the soil with an overhead Mandel track
sprayer equipped with a 8002E nozzles calibrated to deliver 187
L/ha over an application area of 0.503 m.sup.2 at a spray height of
18 inches (46 cm) above average pot height. Control pots were
sprayed in the same manner with the solvent blank.
[0303] The treated and control pots were placed in a greenhouse and
top watered as needed. When required to ensure good germination and
healthy plants, a fungicide treatment and/or other chemical or
physical treatment was applied. The pots were maintained in a
greenhouse with an approximate 14 hr photoperiod which was
maintained at about 29.degree. C. during the day and 26.degree. C.
during the night. Nutrients (Peters.RTM. Excel 15-5-15 5-Ca 2-Mg)
were applied in the irrigation solution as needed and water was
added on a regular basis. Supplemental lighting was provided with
overhead metal halide 1000-Watt lamps as necessary. After
approximately 4 weeks, the condition of the test plants as compared
with that of the untreated plants was determined visually and
scored on a scale of 0 to 100 percent where 0 corresponds to no
injury or growth inhibition and 100 corresponds to complete
kill.
[0304] Colby's equation was used to determine the herbicidal
effects expected from the mixtures (Colby, S. R. 1967. Calculation
of the synergistic and antagonistic response of herbicide
combinations. Weeds 15:20-22.).
[0305] The following equation was used to calculate the expected
activity of mixtures containing two active ingredients, A and
B:
Expected=A+B-(A.times.B/100)
[0306] A=observed efficacy of active ingredient A at the same
concentration as used in the mixture.
[0307] B=observed efficacy of active ingredient B at the same
concentration as used in the mixture.
[0308] Some of the compounds tested, application rates employed,
plant species tested, and results are given in Table 59.
TABLE-US-00065 TABLE 59 Synergistic Activity of Soil-applied,
Pre-emergence Applications of Compound A Benzyl Ester and
Flazasulfuron Herbicidal Compositions on Weed Control Visual Weed
Compound Control (%) - 27 A Benzyl DAA Ester Flazasulfuron SETFA
gae/ha gai/ha Obs Exp 16 0 8 -- 32 0 15 -- 0 25 62 -- 16 25 82 65
32 25 92 67
TABLE-US-00066 SETFA Setaria faberi Herrm. foxtail, giant gae/ha =
grams acid equivalent per hectare gai/ha = grams active ingredient
per hectare Obs = observed value Exp = expected value as calculated
by Colby's equation DAA = days after application
* * * * *